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Wednesday August 19, 2026
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10:00 AM - 12:00 PM
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"Simply Sail" Private Lessons - Simply Sail with Louise - Wednesday August 19th - 10 AM - noon
Simply Sail: A private sailing experience
Offered from June through late August, is a two hour private sailing experience for up to 4 participants per boat/booking. Instruction is offered in your choice of a Catboat or Flying Scot and will be skippered by an experienced sailor. This is an opportunity to enjoy Pleasant Bay while getting an introduction to the basics of sailing–perfect for groups of friends or families!
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Weekday Afternoon Catboat Rentals 8/17 to 8/21
Notices:- Rentals will be unavailable on Saturday 8/22. We will be participating in the Arey's Pond Cat Gathering. Please contact Peter Grumbling (catboats@pbcb.cc) to inquire about sailing in the APCG. We will be open as usual on Sunday 8/23.- For the month of August, rental spots will be opened week by week. You can sign up for time slots beginning the week prior on Monday at 8 AM, similar to the racing sign-ups.Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Weekday Afternoon Flying Scot Rentals 8/17 to 8/21
Notices:- Rentals will be unavailable on Saturday 8/22. We will be participating in the Arey's Pond Cat Gathering. Please contact Peter Grumbling (catboats@pbcb.cc) to inquire about sailing in the APCG. We will be open as usual on Sunday 8/23.- For the month of August, rental spots will be opened week by week. You can sign up for time slots beginning the week prior on Monday at 8 AM, similar to the racing sign-ups.Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Women on the Water (WOW) - Women on the Water August 17th - August 20th Afternoons (Sue + Louise)
Registration for all 2026 Women on the Water program classes will open on Tuesday, February 24th at 10 AM.
PBCB’s “Women on the Water” is a unique sailing program designed and taught by women, for women. Our goal is to provide welcoming and accessible opportunities—no experience necessary. We welcome beginners, those returning to the sport, and returning Women on the Water participants looking to challenge themselves. Classes are hands-on and focus on building self-reliance, independence, teamwork, resourcefulness, and critical thinking skills in a supportive, on-the-water learning environment. Participants will learn and practice fundamental sailing skills, including basic seamanship, sailing terminology and parts of the boat, boat handling and maneuvers, points of sail, knot-tying, and on-the-water communication. Classes begin in June and run through late August. We provide the boats, materials, and instructors—we just need you! Each session includes a brief chalk talk lesson followed by approximately two hours of sailing on beautiful Pleasant Bay. Through a generous donation from a local family foundation, scholarships are available for this program.Click the link below to apply for a WOW Scholarship!If you are not applying for a scholarship full payment is required when registering..
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1:30 PM - 2:30 PM
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Parent Friend Trip - Sailing and Science Parent Friend Trip Wednesday August 19th 1:30pm
Parent Observation Boat Ride aboard FRIENDJoin us aboard FRIEND our 37 foot electric, solar powered pontoon boat for a unique opportunity to watch your child participate in their sailing lesson from the water. This guided boat ride allows parents and family members to experience the excitement of the program while observing instruction, skill development, and the confidence students gain on the water.Our experienced captain will position the boat to provide excellent viewing while maintaining a safe distance from the lesson area. Along the way, you'll learn more about our sailing program, the boats your child is sailing, and how our instructors help students build skills and independence.This is a wonderful way to share in your child's sailing experience, capture memorable photos, and enjoy the beauty of Pleasant Bay.Please Note:
Space is limited and advance reservations are required.
Children participating in lessons must remain with their instructors and may not ride on the observation boat during the lesson.
The boat ride is weather dependent and may be rescheduled or canceled if conditions are unsafe.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Weekday Evening Catboat Rentals 8/17 to 8/21
Notices:- Rentals will be unavailable on Saturday 8/22. We will be participating in the Arey's Pond Cat Gathering. Please contact Peter Grumbling (catboats@pbcb.cc) to inquire about sailing in the APCG. We will be open as usual on Sunday 8/23.- For the month of August, rental spots will be opened week by week. You can sign up for time slots beginning the week prior on Monday at 8 AM, similar to the racing sign-ups.Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Weekday Evening Scots Rentals 8/17 to 8/21
Notices:- Rentals will be unavailable on Saturday 8/22. We will be participating in the Arey's Pond Cat Gathering. Please contact Peter Grumbling (catboats@pbcb.cc) to inquire about sailing in the APCG. We will be open as usual on Sunday 8/23.- For the month of August, rental spots will be opened week by week. You can sign up for time slots beginning the week prior on Monday at 8 AM, similar to the racing sign-ups.Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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Thursday August 20, 2026
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Weekday Afternoon Catboat Rentals 8/17 to 8/21
Notices:- Rentals will be unavailable on Saturday 8/22. We will be participating in the Arey's Pond Cat Gathering. Please contact Peter Grumbling (catboats@pbcb.cc) to inquire about sailing in the APCG. We will be open as usual on Sunday 8/23.- For the month of August, rental spots will be opened week by week. You can sign up for time slots beginning the week prior on Monday at 8 AM, similar to the racing sign-ups.Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Weekday Afternoon Flying Scot Rentals 8/17 to 8/21
Notices:- Rentals will be unavailable on Saturday 8/22. We will be participating in the Arey's Pond Cat Gathering. Please contact Peter Grumbling (catboats@pbcb.cc) to inquire about sailing in the APCG. We will be open as usual on Sunday 8/23.- For the month of August, rental spots will be opened week by week. You can sign up for time slots beginning the week prior on Monday at 8 AM, similar to the racing sign-ups.Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Women on the Water (WOW) - Women on the Water August 17th - August 20th Afternoons (Sue + Louise)
Registration for all 2026 Women on the Water program classes will open on Tuesday, February 24th at 10 AM.
PBCB’s “Women on the Water” is a unique sailing program designed and taught by women, for women. Our goal is to provide welcoming and accessible opportunities—no experience necessary. We welcome beginners, those returning to the sport, and returning Women on the Water participants looking to challenge themselves. Classes are hands-on and focus on building self-reliance, independence, teamwork, resourcefulness, and critical thinking skills in a supportive, on-the-water learning environment. Participants will learn and practice fundamental sailing skills, including basic seamanship, sailing terminology and parts of the boat, boat handling and maneuvers, points of sail, knot-tying, and on-the-water communication. Classes begin in June and run through late August. We provide the boats, materials, and instructors—we just need you! Each session includes a brief chalk talk lesson followed by approximately two hours of sailing on beautiful Pleasant Bay. Through a generous donation from a local family foundation, scholarships are available for this program.Click the link below to apply for a WOW Scholarship!If you are not applying for a scholarship full payment is required when registering..
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Weekday Evening Catboat Rentals 8/17 to 8/21
Notices:- Rentals will be unavailable on Saturday 8/22. We will be participating in the Arey's Pond Cat Gathering. Please contact Peter Grumbling (catboats@pbcb.cc) to inquire about sailing in the APCG. We will be open as usual on Sunday 8/23.- For the month of August, rental spots will be opened week by week. You can sign up for time slots beginning the week prior on Monday at 8 AM, similar to the racing sign-ups.Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Weekday Evening Scots Rentals 8/17 to 8/21
Notices:- Rentals will be unavailable on Saturday 8/22. We will be participating in the Arey's Pond Cat Gathering. Please contact Peter Grumbling (catboats@pbcb.cc) to inquire about sailing in the APCG. We will be open as usual on Sunday 8/23.- For the month of August, rental spots will be opened week by week. You can sign up for time slots beginning the week prior on Monday at 8 AM, similar to the racing sign-ups.Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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Friday August 21, 2026
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Weekday Afternoon Catboat Rentals 8/17 to 8/21
Notices:- Rentals will be unavailable on Saturday 8/22. We will be participating in the Arey's Pond Cat Gathering. Please contact Peter Grumbling (catboats@pbcb.cc) to inquire about sailing in the APCG. We will be open as usual on Sunday 8/23.- For the month of August, rental spots will be opened week by week. You can sign up for time slots beginning the week prior on Monday at 8 AM, similar to the racing sign-ups.Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Weekday Afternoon Flying Scot Rentals 8/17 to 8/21
Notices:- Rentals will be unavailable on Saturday 8/22. We will be participating in the Arey's Pond Cat Gathering. Please contact Peter Grumbling (catboats@pbcb.cc) to inquire about sailing in the APCG. We will be open as usual on Sunday 8/23.- For the month of August, rental spots will be opened week by week. You can sign up for time slots beginning the week prior on Monday at 8 AM, similar to the racing sign-ups.Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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4:15 PM - 7:00 PM
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Friday Night Friendly CATBOAT Races - August 21st CREW
Racing is a fun and challenging way to get more out of the sport of sailing. It provides an opportunity to reinforce and build your sailing skills while becoming part of a friendly community. Fine tune your boat handling skills through friendly competition. Skills checked sailors that have purchased a RACE PASS are welcome to skipper. If you wish to bring a crew that is also a skills checked sailor they as well need to have a RACE PASS, please have the sign up individually as "skills checked crew"Registration for each week will open the Monday prior to the race.You must sign up for each individual race you would like to participate in. Skills checked pass holders who want to crew and do not have a specified skipper are also welcome. Please also sign up as "skills checked crew". A Skipper's meeting will be held at 4:15 PM on the dock and all crew should be ready to go out by 4:30 PM. We will race until approximately 7 PM. Directly following the races, please join us on the bluff for a complimentary BBQ. PBCB will supply hamburgers, cheese, hot dogs, rolls, chips, paper products/cutlery, and condiments. Please feel free to bring your own beverages and/or a side to share. Post BBQ clean up will be a group effort.
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4:15 PM - 7:00 PM
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Friday Night Friendly CATBOAT Races - August 21st SKIPPER
Racing is a fun and challenging way to get more out of the sport of sailing. It provides an opportunity to reinforce and build your sailing skills while becoming part of a friendly community. Fine tune your boat handling skills through friendly competition. Skills checked sailors that have purchased a RACE PASS are welcome to skipper. If you wish to bring a crew that is also a skills checked sailor they as well need to have a RACE PASS, please have the sign up individually as "skills checked crew"Registration for each week will open the Monday prior to the race.You must sign up for each individual race you would like to participate in. Skills checked pass holders who want to crew and do not have a specified skipper are also welcome. Please also sign up as "skills checked crew". A Skipper's meeting will be held at 4:15 PM on the dock and all crew should be ready to go out by 4:30 PM. We will race until approximately 7 PM. Directly following the races, please join us on the bluff for a complimentary BBQ. PBCB will supply hamburgers, cheese, hot dogs, rolls, chips, paper products/cutlery, and condiments. Please feel free to bring your own beverages and/or a side to share. Post BBQ clean up will be a group effort.
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4:15 PM - 7:00 PM
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Friday Night Friendly FLYING SCOT Races - August 21st CREW
Racing is a fun and challenging way to get more out of the sport of sailing. It provides an opportunity to reinforce and build your sailing skills while becoming part of a friendly community. Fine tune your boat handling skills through friendly competition. Skills checked sailors that have purchased a RACE PASS are welcome to skipper. If you wish to bring a crew that is also a skills checked sailor they as well need to have a RACE PASS, please have the sign up individually as "skills checked crew"Registration for each week will open the Monday prior to the race.You must sign up for each individual race you would like to participate in. Skills checked pass holders who want to crew and do not have a specified skipper are also welcome. Please also sign up as "skills checked crew". A Skipper's meeting will be held at 4:15 PM on the dock and all crew should be ready to go out by 4:30 PM. We will race until approximately 7 PM. Directly following the races, please join us on the bluff for a complimentary BBQ. PBCB will supply hamburgers, cheese, hot dogs, rolls, chips, paper products/cutlery, and condiments. Please feel free to bring your own beverages and/or a side to share. Post BBQ clean up will be a group effort.
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4:15 PM - 7:00 PM
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Friday Night Friendly FLYING SCOT Races - August 21st SKIPPER
Racing is a fun and challenging way to get more out of the sport of sailing. It provides an opportunity to reinforce and build your sailing skills while becoming part of a friendly community. Fine tune your boat handling skills through friendly competition. Skills checked sailors that have purchased a RACE PASS are welcome to skipper. If you wish to bring a crew that is also a skills checked sailor they as well need to have a RACE PASS, please have the sign up individually as "skills checked crew"Registration for each week will open the Monday prior to the race.You must sign up for each individual race you would like to participate in. Skills checked pass holders who want to crew and do not have a specified skipper are also welcome. Please also sign up as "skills checked crew". A Skipper's meeting will be held at 4:15 PM on the dock and all crew should be ready to go out by 4:30 PM. We will race until approximately 7 PM. Directly following the races, please join us on the bluff for a complimentary BBQ. PBCB will supply hamburgers, cheese, hot dogs, rolls, chips, paper products/cutlery, and condiments. Please feel free to bring your own beverages and/or a side to share. Post BBQ clean up will be a group effort.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Weekday Evening Scots Rentals 8/17 to 8/21
Notices:- Rentals will be unavailable on Saturday 8/22. We will be participating in the Arey's Pond Cat Gathering. Please contact Peter Grumbling (catboats@pbcb.cc) to inquire about sailing in the APCG. We will be open as usual on Sunday 8/23.- For the month of August, rental spots will be opened week by week. You can sign up for time slots beginning the week prior on Monday at 8 AM, similar to the racing sign-ups.Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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Sunday August 23, 2026
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Weekend Afternoon Catboat Rentals 8/23
Notices:- Rentals will be unavailable on Saturday 8/22. We will be participating in the Arey's Pond Cat Gathering. Please contact Peter Grumbling (catboats@pbcb.cc) to inquire about sailing in the APCG. We will be open as usual on Sunday 8/23.- For the month of August, rental spots will be opened week by week. You can sign up for time slots beginning the week prior on Monday at 8 AM, similar to the racing sign-ups.Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Weekend Afternoon Flying Scot Rentals 8/23
Notices:- Rentals will be unavailable on Saturday 8/22. We will be participating in the Arey's Pond Cat Gathering. Please contact Peter Grumbling (catboats@pbcb.cc) to inquire about sailing in the APCG. We will be open as usual on Sunday 8/23.- For the month of August, rental spots will be opened week by week. You can sign up for time slots beginning the week prior on Monday at 8 AM, similar to the racing sign-ups.Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Weekend Evening Catboat Rentals 8/23
Notices:- Rentals will be unavailable on Saturday 8/22. We will be participating in the Arey's Pond Cat Gathering. Please contact Peter Grumbling (catboats@pbcb.cc) to inquire about sailing in the APCG. We will be open as usual on Sunday 8/23.- For the month of August, rental spots will be opened week by week. You can sign up for time slots beginning the week prior on Monday at 8 AM, similar to the racing sign-ups.Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Weekend Evening Flying Scot Rentals 8/23
Notices:- Rentals will be unavailable on Saturday 8/22. We will be participating in the Arey's Pond Cat Gathering. Please contact Peter Grumbling (catboats@pbcb.cc) to inquire about sailing in the APCG. We will be open as usual on Sunday 8/23.- For the month of August, rental spots will be opened week by week. You can sign up for time slots beginning the week prior on Monday at 8 AM, similar to the racing sign-ups.Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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Monday August 24, 2026
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9:00 AM - 11:30 AM
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Adult Catboat Sailing Lessons - Adult Catboat Class August 24th-August 27th Mornings
Using the uniquely versatile catboat as our vessel of choice, the Catboat Program focuses on developing sailing skills through a series of courses designed to help participants reach their potential regardless of their previous experience. The Catboat Program began in 2019 by Suzanne Leahy, who brought her love of sailing and catboats together to create a community of PBCB catboaters. Peter Grumbling will succeed Suzanne as Catboat Program Coordinator. Peter has been instrumental in growing the program to what it is today as it continues to evolve to include classes encompassing all levels, a Friday racing series, participation in sailing events and Bay-wide catboat cruises; the goal of the program is to foster independence and confidence. Participants will learn and practice fundamental sailing skills, including basic seamanship, sailing terminology and parts of the boat, boat handling and maneuvers, points of sail, knots and teamwork. Our instructors are knowledgeable and adept at teaching to each participant’s needs. Each class consists of one instructor and two participants per boat, rotating instructors throughout the week, which adds to your experience of teaching and sailing styles.Our fleet of Marshall Sandpipers is the foundation of the program. They are a versatile teaching boat having all the wonderful catboat characteristics: stability, large cockpit and ability to shorten sail. Our fleet is well-maintained, and all equipment is updated annually as needed. It is from this solid foundation that our instructors can successfully teach!Catboat classes and programs are open to adults 18 years or older and run from mid-June through August. Classes will meet in the catboat shop (the garage doors are directly next to our parking lot).
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9:30 AM - 3:00 PM
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Sailing and Science: Last Days on the Bay! - Sailing and Science: Last Days on the Bay! Ages 7-10, 8/24 - 8/28, 930am to 3pm
The Sailing & Science Camp: Last Days on the Bay! mirrors our summer Science & Sailing program, extended for 2 additional weeks and with just 1 age group (ages 7-10). This program pairs a half day of discovery science and exploration with a half day of sailing.During science class campers may travel to Sipson or Strong Island to explore marine habitats, observe wildlife on our cranberry bog nature walks, conduct classroom experiments, play games, and enjoy a trip on our floating classroom, the Friend. On the water, campers will be sailing in Flying Scot sailboats and learning basic sailing skills. Topics covered will be safety on the water, reading the wind, parts of the boat and sail, rigging, mooring procedures, steering, tacking and jibing.
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10:00 AM - 12:30 PM
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Women on the Water (WOW) - Women on the Water August 24th - August 27th Mornings (Sue + Abby)
Registration for all 2026 Women on the Water program classes will open on Tuesday, February 24th at 10 AM.
PBCB’s “Women on the Water” is a unique sailing program designed and taught by women, for women. Our goal is to provide welcoming and accessible opportunities—no experience necessary. We welcome beginners, those returning to the sport, and returning Women on the Water participants looking to challenge themselves. Classes are hands-on and focus on building self-reliance, independence, teamwork, resourcefulness, and critical thinking skills in a supportive, on-the-water learning environment. Participants will learn and practice fundamental sailing skills, including basic seamanship, sailing terminology and parts of the boat, boat handling and maneuvers, points of sail, knot-tying, and on-the-water communication. Classes begin in June and run through late August. We provide the boats, materials, and instructors—we just need you! Each session includes a brief chalk talk lesson followed by approximately two hours of sailing on beautiful Pleasant Bay. Through a generous donation from a local family foundation, scholarships are available for this program.Click the link below to apply for a WOW Scholarship!If you are not applying for a scholarship full payment is required when registering..
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12:30 PM - 3:00 PM
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Adult Catboat Sailing Lessons - Adult Catboat Class August 24th-August 27th Afternoons
Using the uniquely versatile catboat as our vessel of choice, the Catboat Program focuses on developing sailing skills through a series of courses designed to help participants reach their potential regardless of their previous experience. The Catboat Program began in 2019 by Suzanne Leahy, who brought her love of sailing and catboats together to create a community of PBCB catboaters. Peter Grumbling will succeed Suzanne as Catboat Program Coordinator. Peter has been instrumental in growing the program to what it is today as it continues to evolve to include classes encompassing all levels, a Friday racing series, participation in sailing events and Bay-wide catboat cruises; the goal of the program is to foster independence and confidence. Participants will learn and practice fundamental sailing skills, including basic seamanship, sailing terminology and parts of the boat, boat handling and maneuvers, points of sail, knots and teamwork. Our instructors are knowledgeable and adept at teaching to each participant’s needs. Each class consists of one instructor and two participants per boat, rotating instructors throughout the week, which adds to your experience of teaching and sailing styles.Our fleet of Marshall Sandpipers is the foundation of the program. They are a versatile teaching boat having all the wonderful catboat characteristics: stability, large cockpit and ability to shorten sail. Our fleet is well-maintained, and all equipment is updated annually as needed. It is from this solid foundation that our instructors can successfully teach!Catboat classes and programs are open to adults 18 years or older and run from mid-June through August. Classes will meet in the catboat shop (the garage doors are directly next to our parking lot).
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Weekday Afternoon Catboat Rentals 8/24 to 8/28
Notices:- Rentals will be unavailable on Saturday 8/22. We will be participating in the Arey's Pond Cat Gathering. Please contact Peter Grumbling (catboats@pbcb.cc) to inquire about sailing in the APCG. We will be open as usual on Sunday 8/23.- For the month of August, rental spots will be opened week by week. You can sign up for time slots beginning the week prior on Monday at 8 AM, similar to the racing sign-ups.Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Weekday Afternoon Flying Scot Rentals 8/24 to 8/28
Notices:- Rentals will be unavailable on Saturday 8/22. We will be participating in the Arey's Pond Cat Gathering. Please contact Peter Grumbling (catboats@pbcb.cc) to inquire about sailing in the APCG. We will be open as usual on Sunday 8/23.- For the month of August, rental spots will be opened week by week. You can sign up for time slots beginning the week prior on Monday at 8 AM, similar to the racing sign-ups.Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Weekday Evening Catboat Rentals August 24th through 28th
Notices:- Rentals will be unavailable on Saturday 8/22. We will be participating in the Arey's Pond Cat Gathering. Please contact Peter Grumbling (catboats@pbcb.cc) to inquire about sailing in the APCG. We will be open as usual on Sunday 8/23.- For the month of August, rental spots will be opened week by week. You can sign up for time slots beginning the week prior on Monday at 8 AM, similar to the racing sign-ups.Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Weekday Evening Flying Scot Rentals August 24th-August 28th
Notices:- Rentals will be unavailable on Saturday 8/22. We will be participating in the Arey's Pond Cat Gathering. Please contact Peter Grumbling (catboats@pbcb.cc) to inquire about sailing in the APCG. We will be open as usual on Sunday 8/23.- For the month of August, rental spots will be opened week by week. You can sign up for time slots beginning the week prior on Monday at 8 AM, similar to the racing sign-ups.Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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Tuesday August 25, 2026
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9:00 AM - 11:30 AM
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Adult Catboat Sailing Lessons - Adult Catboat Class August 24th-August 27th Mornings
Using the uniquely versatile catboat as our vessel of choice, the Catboat Program focuses on developing sailing skills through a series of courses designed to help participants reach their potential regardless of their previous experience. The Catboat Program began in 2019 by Suzanne Leahy, who brought her love of sailing and catboats together to create a community of PBCB catboaters. Peter Grumbling will succeed Suzanne as Catboat Program Coordinator. Peter has been instrumental in growing the program to what it is today as it continues to evolve to include classes encompassing all levels, a Friday racing series, participation in sailing events and Bay-wide catboat cruises; the goal of the program is to foster independence and confidence. Participants will learn and practice fundamental sailing skills, including basic seamanship, sailing terminology and parts of the boat, boat handling and maneuvers, points of sail, knots and teamwork. Our instructors are knowledgeable and adept at teaching to each participant’s needs. Each class consists of one instructor and two participants per boat, rotating instructors throughout the week, which adds to your experience of teaching and sailing styles.Our fleet of Marshall Sandpipers is the foundation of the program. They are a versatile teaching boat having all the wonderful catboat characteristics: stability, large cockpit and ability to shorten sail. Our fleet is well-maintained, and all equipment is updated annually as needed. It is from this solid foundation that our instructors can successfully teach!Catboat classes and programs are open to adults 18 years or older and run from mid-June through August. Classes will meet in the catboat shop (the garage doors are directly next to our parking lot).
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9:30 AM - 3:00 PM
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Sailing and Science: Last Days on the Bay! - Sailing and Science: Last Days on the Bay! Ages 7-10, 8/24 - 8/28, 930am to 3pm
The Sailing & Science Camp: Last Days on the Bay! mirrors our summer Science & Sailing program, extended for 2 additional weeks and with just 1 age group (ages 7-10). This program pairs a half day of discovery science and exploration with a half day of sailing.During science class campers may travel to Sipson or Strong Island to explore marine habitats, observe wildlife on our cranberry bog nature walks, conduct classroom experiments, play games, and enjoy a trip on our floating classroom, the Friend. On the water, campers will be sailing in Flying Scot sailboats and learning basic sailing skills. Topics covered will be safety on the water, reading the wind, parts of the boat and sail, rigging, mooring procedures, steering, tacking and jibing.
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10:00 AM - 12:30 PM
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Women on the Water (WOW) - Women on the Water August 24th - August 27th Mornings (Sue + Abby)
Registration for all 2026 Women on the Water program classes will open on Tuesday, February 24th at 10 AM.
PBCB’s “Women on the Water” is a unique sailing program designed and taught by women, for women. Our goal is to provide welcoming and accessible opportunities—no experience necessary. We welcome beginners, those returning to the sport, and returning Women on the Water participants looking to challenge themselves. Classes are hands-on and focus on building self-reliance, independence, teamwork, resourcefulness, and critical thinking skills in a supportive, on-the-water learning environment. Participants will learn and practice fundamental sailing skills, including basic seamanship, sailing terminology and parts of the boat, boat handling and maneuvers, points of sail, knot-tying, and on-the-water communication. Classes begin in June and run through late August. We provide the boats, materials, and instructors—we just need you! Each session includes a brief chalk talk lesson followed by approximately two hours of sailing on beautiful Pleasant Bay. Through a generous donation from a local family foundation, scholarships are available for this program.Click the link below to apply for a WOW Scholarship!If you are not applying for a scholarship full payment is required when registering..
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12:30 PM - 3:00 PM
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Adult Catboat Sailing Lessons - Adult Catboat Class August 24th-August 27th Afternoons
Using the uniquely versatile catboat as our vessel of choice, the Catboat Program focuses on developing sailing skills through a series of courses designed to help participants reach their potential regardless of their previous experience. The Catboat Program began in 2019 by Suzanne Leahy, who brought her love of sailing and catboats together to create a community of PBCB catboaters. Peter Grumbling will succeed Suzanne as Catboat Program Coordinator. Peter has been instrumental in growing the program to what it is today as it continues to evolve to include classes encompassing all levels, a Friday racing series, participation in sailing events and Bay-wide catboat cruises; the goal of the program is to foster independence and confidence. Participants will learn and practice fundamental sailing skills, including basic seamanship, sailing terminology and parts of the boat, boat handling and maneuvers, points of sail, knots and teamwork. Our instructors are knowledgeable and adept at teaching to each participant’s needs. Each class consists of one instructor and two participants per boat, rotating instructors throughout the week, which adds to your experience of teaching and sailing styles.Our fleet of Marshall Sandpipers is the foundation of the program. They are a versatile teaching boat having all the wonderful catboat characteristics: stability, large cockpit and ability to shorten sail. Our fleet is well-maintained, and all equipment is updated annually as needed. It is from this solid foundation that our instructors can successfully teach!Catboat classes and programs are open to adults 18 years or older and run from mid-June through August. Classes will meet in the catboat shop (the garage doors are directly next to our parking lot).
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Weekday Afternoon Catboat Rentals 8/24 to 8/28
Notices:- Rentals will be unavailable on Saturday 8/22. We will be participating in the Arey's Pond Cat Gathering. Please contact Peter Grumbling (catboats@pbcb.cc) to inquire about sailing in the APCG. We will be open as usual on Sunday 8/23.- For the month of August, rental spots will be opened week by week. You can sign up for time slots beginning the week prior on Monday at 8 AM, similar to the racing sign-ups.Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Weekday Afternoon Flying Scot Rentals 8/24 to 8/28
Notices:- Rentals will be unavailable on Saturday 8/22. We will be participating in the Arey's Pond Cat Gathering. Please contact Peter Grumbling (catboats@pbcb.cc) to inquire about sailing in the APCG. We will be open as usual on Sunday 8/23.- For the month of August, rental spots will be opened week by week. You can sign up for time slots beginning the week prior on Monday at 8 AM, similar to the racing sign-ups.Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Weekday Evening Catboat Rentals August 24th through 28th
Notices:- Rentals will be unavailable on Saturday 8/22. We will be participating in the Arey's Pond Cat Gathering. Please contact Peter Grumbling (catboats@pbcb.cc) to inquire about sailing in the APCG. We will be open as usual on Sunday 8/23.- For the month of August, rental spots will be opened week by week. You can sign up for time slots beginning the week prior on Monday at 8 AM, similar to the racing sign-ups.Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Weekday Evening Flying Scot Rentals August 24th-August 28th
Notices:- Rentals will be unavailable on Saturday 8/22. We will be participating in the Arey's Pond Cat Gathering. Please contact Peter Grumbling (catboats@pbcb.cc) to inquire about sailing in the APCG. We will be open as usual on Sunday 8/23.- For the month of August, rental spots will be opened week by week. You can sign up for time slots beginning the week prior on Monday at 8 AM, similar to the racing sign-ups.Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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Wednesday August 26, 2026
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9:00 AM - 11:30 AM
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Adult Catboat Sailing Lessons - Adult Catboat Class August 24th-August 27th Mornings
Using the uniquely versatile catboat as our vessel of choice, the Catboat Program focuses on developing sailing skills through a series of courses designed to help participants reach their potential regardless of their previous experience. The Catboat Program began in 2019 by Suzanne Leahy, who brought her love of sailing and catboats together to create a community of PBCB catboaters. Peter Grumbling will succeed Suzanne as Catboat Program Coordinator. Peter has been instrumental in growing the program to what it is today as it continues to evolve to include classes encompassing all levels, a Friday racing series, participation in sailing events and Bay-wide catboat cruises; the goal of the program is to foster independence and confidence. Participants will learn and practice fundamental sailing skills, including basic seamanship, sailing terminology and parts of the boat, boat handling and maneuvers, points of sail, knots and teamwork. Our instructors are knowledgeable and adept at teaching to each participant’s needs. Each class consists of one instructor and two participants per boat, rotating instructors throughout the week, which adds to your experience of teaching and sailing styles.Our fleet of Marshall Sandpipers is the foundation of the program. They are a versatile teaching boat having all the wonderful catboat characteristics: stability, large cockpit and ability to shorten sail. Our fleet is well-maintained, and all equipment is updated annually as needed. It is from this solid foundation that our instructors can successfully teach!Catboat classes and programs are open to adults 18 years or older and run from mid-June through August. Classes will meet in the catboat shop (the garage doors are directly next to our parking lot).
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9:30 AM - 3:00 PM
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Sailing and Science: Last Days on the Bay! - Sailing and Science: Last Days on the Bay! Ages 7-10, 8/24 - 8/28, 930am to 3pm
The Sailing & Science Camp: Last Days on the Bay! mirrors our summer Science & Sailing program, extended for 2 additional weeks and with just 1 age group (ages 7-10). This program pairs a half day of discovery science and exploration with a half day of sailing.During science class campers may travel to Sipson or Strong Island to explore marine habitats, observe wildlife on our cranberry bog nature walks, conduct classroom experiments, play games, and enjoy a trip on our floating classroom, the Friend. On the water, campers will be sailing in Flying Scot sailboats and learning basic sailing skills. Topics covered will be safety on the water, reading the wind, parts of the boat and sail, rigging, mooring procedures, steering, tacking and jibing.
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10:00 AM - 12:30 PM
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Women on the Water (WOW) - Women on the Water August 24th - August 27th Mornings (Sue + Abby)
Registration for all 2026 Women on the Water program classes will open on Tuesday, February 24th at 10 AM.
PBCB’s “Women on the Water” is a unique sailing program designed and taught by women, for women. Our goal is to provide welcoming and accessible opportunities—no experience necessary. We welcome beginners, those returning to the sport, and returning Women on the Water participants looking to challenge themselves. Classes are hands-on and focus on building self-reliance, independence, teamwork, resourcefulness, and critical thinking skills in a supportive, on-the-water learning environment. Participants will learn and practice fundamental sailing skills, including basic seamanship, sailing terminology and parts of the boat, boat handling and maneuvers, points of sail, knot-tying, and on-the-water communication. Classes begin in June and run through late August. We provide the boats, materials, and instructors—we just need you! Each session includes a brief chalk talk lesson followed by approximately two hours of sailing on beautiful Pleasant Bay. Through a generous donation from a local family foundation, scholarships are available for this program.Click the link below to apply for a WOW Scholarship!If you are not applying for a scholarship full payment is required when registering..
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12:30 PM - 3:00 PM
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Adult Catboat Sailing Lessons - Adult Catboat Class August 24th-August 27th Afternoons
Using the uniquely versatile catboat as our vessel of choice, the Catboat Program focuses on developing sailing skills through a series of courses designed to help participants reach their potential regardless of their previous experience. The Catboat Program began in 2019 by Suzanne Leahy, who brought her love of sailing and catboats together to create a community of PBCB catboaters. Peter Grumbling will succeed Suzanne as Catboat Program Coordinator. Peter has been instrumental in growing the program to what it is today as it continues to evolve to include classes encompassing all levels, a Friday racing series, participation in sailing events and Bay-wide catboat cruises; the goal of the program is to foster independence and confidence. Participants will learn and practice fundamental sailing skills, including basic seamanship, sailing terminology and parts of the boat, boat handling and maneuvers, points of sail, knots and teamwork. Our instructors are knowledgeable and adept at teaching to each participant’s needs. Each class consists of one instructor and two participants per boat, rotating instructors throughout the week, which adds to your experience of teaching and sailing styles.Our fleet of Marshall Sandpipers is the foundation of the program. They are a versatile teaching boat having all the wonderful catboat characteristics: stability, large cockpit and ability to shorten sail. Our fleet is well-maintained, and all equipment is updated annually as needed. It is from this solid foundation that our instructors can successfully teach!Catboat classes and programs are open to adults 18 years or older and run from mid-June through August. Classes will meet in the catboat shop (the garage doors are directly next to our parking lot).
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Weekday Afternoon Catboat Rentals 8/24 to 8/28
Notices:- Rentals will be unavailable on Saturday 8/22. We will be participating in the Arey's Pond Cat Gathering. Please contact Peter Grumbling (catboats@pbcb.cc) to inquire about sailing in the APCG. We will be open as usual on Sunday 8/23.- For the month of August, rental spots will be opened week by week. You can sign up for time slots beginning the week prior on Monday at 8 AM, similar to the racing sign-ups.Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Weekday Afternoon Flying Scot Rentals 8/24 to 8/28
Notices:- Rentals will be unavailable on Saturday 8/22. We will be participating in the Arey's Pond Cat Gathering. Please contact Peter Grumbling (catboats@pbcb.cc) to inquire about sailing in the APCG. We will be open as usual on Sunday 8/23.- For the month of August, rental spots will be opened week by week. You can sign up for time slots beginning the week prior on Monday at 8 AM, similar to the racing sign-ups.Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Weekday Evening Catboat Rentals August 24th through 28th
Notices:- Rentals will be unavailable on Saturday 8/22. We will be participating in the Arey's Pond Cat Gathering. Please contact Peter Grumbling (catboats@pbcb.cc) to inquire about sailing in the APCG. We will be open as usual on Sunday 8/23.- For the month of August, rental spots will be opened week by week. You can sign up for time slots beginning the week prior on Monday at 8 AM, similar to the racing sign-ups.Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Weekday Evening Flying Scot Rentals August 24th-August 28th
Notices:- Rentals will be unavailable on Saturday 8/22. We will be participating in the Arey's Pond Cat Gathering. Please contact Peter Grumbling (catboats@pbcb.cc) to inquire about sailing in the APCG. We will be open as usual on Sunday 8/23.- For the month of August, rental spots will be opened week by week. You can sign up for time slots beginning the week prior on Monday at 8 AM, similar to the racing sign-ups.Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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Thursday August 27, 2026
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9:00 AM - 11:30 AM
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Adult Catboat Sailing Lessons - Adult Catboat Class August 24th-August 27th Mornings
Using the uniquely versatile catboat as our vessel of choice, the Catboat Program focuses on developing sailing skills through a series of courses designed to help participants reach their potential regardless of their previous experience. The Catboat Program began in 2019 by Suzanne Leahy, who brought her love of sailing and catboats together to create a community of PBCB catboaters. Peter Grumbling will succeed Suzanne as Catboat Program Coordinator. Peter has been instrumental in growing the program to what it is today as it continues to evolve to include classes encompassing all levels, a Friday racing series, participation in sailing events and Bay-wide catboat cruises; the goal of the program is to foster independence and confidence. Participants will learn and practice fundamental sailing skills, including basic seamanship, sailing terminology and parts of the boat, boat handling and maneuvers, points of sail, knots and teamwork. Our instructors are knowledgeable and adept at teaching to each participant’s needs. Each class consists of one instructor and two participants per boat, rotating instructors throughout the week, which adds to your experience of teaching and sailing styles.Our fleet of Marshall Sandpipers is the foundation of the program. They are a versatile teaching boat having all the wonderful catboat characteristics: stability, large cockpit and ability to shorten sail. Our fleet is well-maintained, and all equipment is updated annually as needed. It is from this solid foundation that our instructors can successfully teach!Catboat classes and programs are open to adults 18 years or older and run from mid-June through August. Classes will meet in the catboat shop (the garage doors are directly next to our parking lot).
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9:30 AM - 3:00 PM
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Sailing and Science: Last Days on the Bay! - Sailing and Science: Last Days on the Bay! Ages 7-10, 8/24 - 8/28, 930am to 3pm
The Sailing & Science Camp: Last Days on the Bay! mirrors our summer Science & Sailing program, extended for 2 additional weeks and with just 1 age group (ages 7-10). This program pairs a half day of discovery science and exploration with a half day of sailing.During science class campers may travel to Sipson or Strong Island to explore marine habitats, observe wildlife on our cranberry bog nature walks, conduct classroom experiments, play games, and enjoy a trip on our floating classroom, the Friend. On the water, campers will be sailing in Flying Scot sailboats and learning basic sailing skills. Topics covered will be safety on the water, reading the wind, parts of the boat and sail, rigging, mooring procedures, steering, tacking and jibing.
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10:00 AM - 12:30 PM
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Women on the Water (WOW) - Women on the Water August 24th - August 27th Mornings (Sue + Abby)
Registration for all 2026 Women on the Water program classes will open on Tuesday, February 24th at 10 AM.
PBCB’s “Women on the Water” is a unique sailing program designed and taught by women, for women. Our goal is to provide welcoming and accessible opportunities—no experience necessary. We welcome beginners, those returning to the sport, and returning Women on the Water participants looking to challenge themselves. Classes are hands-on and focus on building self-reliance, independence, teamwork, resourcefulness, and critical thinking skills in a supportive, on-the-water learning environment. Participants will learn and practice fundamental sailing skills, including basic seamanship, sailing terminology and parts of the boat, boat handling and maneuvers, points of sail, knot-tying, and on-the-water communication. Classes begin in June and run through late August. We provide the boats, materials, and instructors—we just need you! Each session includes a brief chalk talk lesson followed by approximately two hours of sailing on beautiful Pleasant Bay. Through a generous donation from a local family foundation, scholarships are available for this program.Click the link below to apply for a WOW Scholarship!If you are not applying for a scholarship full payment is required when registering..
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12:30 PM - 3:00 PM
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Adult Catboat Sailing Lessons - Adult Catboat Class August 24th-August 27th Afternoons
Using the uniquely versatile catboat as our vessel of choice, the Catboat Program focuses on developing sailing skills through a series of courses designed to help participants reach their potential regardless of their previous experience. The Catboat Program began in 2019 by Suzanne Leahy, who brought her love of sailing and catboats together to create a community of PBCB catboaters. Peter Grumbling will succeed Suzanne as Catboat Program Coordinator. Peter has been instrumental in growing the program to what it is today as it continues to evolve to include classes encompassing all levels, a Friday racing series, participation in sailing events and Bay-wide catboat cruises; the goal of the program is to foster independence and confidence. Participants will learn and practice fundamental sailing skills, including basic seamanship, sailing terminology and parts of the boat, boat handling and maneuvers, points of sail, knots and teamwork. Our instructors are knowledgeable and adept at teaching to each participant’s needs. Each class consists of one instructor and two participants per boat, rotating instructors throughout the week, which adds to your experience of teaching and sailing styles.Our fleet of Marshall Sandpipers is the foundation of the program. They are a versatile teaching boat having all the wonderful catboat characteristics: stability, large cockpit and ability to shorten sail. Our fleet is well-maintained, and all equipment is updated annually as needed. It is from this solid foundation that our instructors can successfully teach!Catboat classes and programs are open to adults 18 years or older and run from mid-June through August. Classes will meet in the catboat shop (the garage doors are directly next to our parking lot).
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1:00 PM - 3:00 PM
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"Simply Sail" Private Lessons - Flying Scot Simply Sail Private Lesson ( AH) Thursday August 27th 100pm
Simply Sail: A private sailing experience
Offered from June through late August, is a two hour private sailing experience for up to 4 participants per boat/booking. Instruction is offered in your choice of a Catboat or Flying Scot and will be skippered by an experienced sailor. This is an opportunity to enjoy Pleasant Bay while getting an introduction to the basics of sailing–perfect for groups of friends or families!
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Weekday Afternoon Catboat Rentals 8/24 to 8/28
Notices:- Rentals will be unavailable on Saturday 8/22. We will be participating in the Arey's Pond Cat Gathering. Please contact Peter Grumbling (catboats@pbcb.cc) to inquire about sailing in the APCG. We will be open as usual on Sunday 8/23.- For the month of August, rental spots will be opened week by week. You can sign up for time slots beginning the week prior on Monday at 8 AM, similar to the racing sign-ups.Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Weekday Afternoon Flying Scot Rentals 8/24 to 8/28
Notices:- Rentals will be unavailable on Saturday 8/22. We will be participating in the Arey's Pond Cat Gathering. Please contact Peter Grumbling (catboats@pbcb.cc) to inquire about sailing in the APCG. We will be open as usual on Sunday 8/23.- For the month of August, rental spots will be opened week by week. You can sign up for time slots beginning the week prior on Monday at 8 AM, similar to the racing sign-ups.Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Weekday Evening Catboat Rentals August 24th through 28th
Notices:- Rentals will be unavailable on Saturday 8/22. We will be participating in the Arey's Pond Cat Gathering. Please contact Peter Grumbling (catboats@pbcb.cc) to inquire about sailing in the APCG. We will be open as usual on Sunday 8/23.- For the month of August, rental spots will be opened week by week. You can sign up for time slots beginning the week prior on Monday at 8 AM, similar to the racing sign-ups.Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Weekday Evening Flying Scot Rentals August 24th-August 28th
Notices:- Rentals will be unavailable on Saturday 8/22. We will be participating in the Arey's Pond Cat Gathering. Please contact Peter Grumbling (catboats@pbcb.cc) to inquire about sailing in the APCG. We will be open as usual on Sunday 8/23.- For the month of August, rental spots will be opened week by week. You can sign up for time slots beginning the week prior on Monday at 8 AM, similar to the racing sign-ups.Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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6:00 PM - 7:00 PM
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From Boat to Table: Rebuilding Cape Cod's Local Seafood System with Brett Tolley - From Boat to Table: Rebuilding Cape Cod's Local Seafood System with Brett Tolley
Join us as we welcome Brett Tolley, co-founder and General Manager of Chatham Harvesters Cooperative, for an engaging discussion about the future of local seafood on Cape Cod. Born into a multi-generation fishing family in Chatham, Brett has dedicated his career to supporting fishing communities, sustainable fisheries, and stronger local food systems.
In this presentation, Brett will share how Chatham Harvesters was founded to help local fishermen take control of their catch, earn fair prices for their work, and reconnect Cape Cod communities with fresh, locally harvested seafood. Guests will learn about the challenges facing today's fishing industry, the importance of supporting working waterfronts, and how choosing local seafood can strengthen the economy, reduce environmental impacts, and support healthy oceans for future generations. Whether you're a seafood lover, environmental advocate, educator, or simply curious about Cape Cod's maritime heritage, this talk offers a unique look into the people and stories behind our local seafood system.
About the Speaker
Brett Tolley is the co-founder and General Manager of Chatham Harvesters Cooperative, Massachusetts' only fisherman-owned and operated seafood cooperative. Raised in Chatham as part of a multi-generation commercial fishing family, Brett has spent his career advocating for healthy marine ecosystems and thriving fishing communities. Before launching Chatham Harvesters, he served for 15 years with the North American Marine Alliance, helping support fishermen and local seafood businesses across the country. Today, Brett leads a cooperative of more than 25 Cape Cod fishing families working together to provide sustainable, locally harvested seafood directly to consumers, schools, and communities throughout the region. Through his work, he continues to champion a seafood system that benefits fishermen, consumers, and the environment alike.
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Friday August 28, 2026
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9:30 AM - 3:00 PM
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Sailing and Science: Last Days on the Bay! - Sailing and Science: Last Days on the Bay! Ages 7-10, 8/24 - 8/28, 930am to 3pm
The Sailing & Science Camp: Last Days on the Bay! mirrors our summer Science & Sailing program, extended for 2 additional weeks and with just 1 age group (ages 7-10). This program pairs a half day of discovery science and exploration with a half day of sailing.During science class campers may travel to Sipson or Strong Island to explore marine habitats, observe wildlife on our cranberry bog nature walks, conduct classroom experiments, play games, and enjoy a trip on our floating classroom, the Friend. On the water, campers will be sailing in Flying Scot sailboats and learning basic sailing skills. Topics covered will be safety on the water, reading the wind, parts of the boat and sail, rigging, mooring procedures, steering, tacking and jibing.
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1:00 PM - 3:00 PM
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"Simply Sail" Private Lessons - Flying Scot Simply Sail Private Lesson ( AH) Friday August 28th 100pm
Simply Sail: A private sailing experience
Offered from June through late August, is a two hour private sailing experience for up to 4 participants per boat/booking. Instruction is offered in your choice of a Catboat or Flying Scot and will be skippered by an experienced sailor. This is an opportunity to enjoy Pleasant Bay while getting an introduction to the basics of sailing–perfect for groups of friends or families!
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Weekday Afternoon Catboat Rentals 8/24 to 8/28
Notices:- Rentals will be unavailable on Saturday 8/22. We will be participating in the Arey's Pond Cat Gathering. Please contact Peter Grumbling (catboats@pbcb.cc) to inquire about sailing in the APCG. We will be open as usual on Sunday 8/23.- For the month of August, rental spots will be opened week by week. You can sign up for time slots beginning the week prior on Monday at 8 AM, similar to the racing sign-ups.Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Weekday Afternoon Flying Scot Rentals 8/24 to 8/28
Notices:- Rentals will be unavailable on Saturday 8/22. We will be participating in the Arey's Pond Cat Gathering. Please contact Peter Grumbling (catboats@pbcb.cc) to inquire about sailing in the APCG. We will be open as usual on Sunday 8/23.- For the month of August, rental spots will be opened week by week. You can sign up for time slots beginning the week prior on Monday at 8 AM, similar to the racing sign-ups.Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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4:15 PM - 7:00 PM
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Friday Night Friendly CATBOAT Races - August 28th CREW
Racing is a fun and challenging way to get more out of the sport of sailing. It provides an opportunity to reinforce and build your sailing skills while becoming part of a friendly community. Fine tune your boat handling skills through friendly competition. Skills checked sailors that have purchased a RACE PASS are welcome to skipper. If you wish to bring a crew that is also a skills checked sailor they as well need to have a RACE PASS, please have the sign up individually as "skills checked crew"Registration for each week will open the Monday prior to the race.You must sign up for each individual race you would like to participate in. Skills checked pass holders who want to crew and do not have a specified skipper are also welcome. Please also sign up as "skills checked crew". A Skipper's meeting will be held at 4:15 PM on the dock and all crew should be ready to go out by 4:30 PM. We will race until approximately 7 PM. Directly following the races, please join us on the bluff for a complimentary BBQ. PBCB will supply hamburgers, cheese, hot dogs, rolls, chips, paper products/cutlery, and condiments. Please feel free to bring your own beverages and/or a side to share. Post BBQ clean up will be a group effort.
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4:15 PM - 7:00 PM
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Friday Night Friendly CATBOAT Races - August 28th SKIPPER
Racing is a fun and challenging way to get more out of the sport of sailing. It provides an opportunity to reinforce and build your sailing skills while becoming part of a friendly community. Fine tune your boat handling skills through friendly competition. Skills checked sailors that have purchased a RACE PASS are welcome to skipper. If you wish to bring a crew that is also a skills checked sailor they as well need to have a RACE PASS, please have the sign up individually as "skills checked crew"Registration for each week will open the Monday prior to the race.You must sign up for each individual race you would like to participate in. Skills checked pass holders who want to crew and do not have a specified skipper are also welcome. Please also sign up as "skills checked crew". A Skipper's meeting will be held at 4:15 PM on the dock and all crew should be ready to go out by 4:30 PM. We will race until approximately 7 PM. Directly following the races, please join us on the bluff for a complimentary BBQ. PBCB will supply hamburgers, cheese, hot dogs, rolls, chips, paper products/cutlery, and condiments. Please feel free to bring your own beverages and/or a side to share. Post BBQ clean up will be a group effort.
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4:15 PM - 7:00 PM
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Friday Night Friendly FLYING SCOT Races - August 28th CREW
Racing is a fun and challenging way to get more out of the sport of sailing. It provides an opportunity to reinforce and build your sailing skills while becoming part of a friendly community. Fine tune your boat handling skills through friendly competition. Skills checked sailors that have purchased a RACE PASS are welcome to skipper. If you wish to bring a crew that is also a skills checked sailor they as well need to have a RACE PASS, please have the sign up individually as "skills checked crew"Registration for each week will open the Monday prior to the race.You must sign up for each individual race you would like to participate in. Skills checked pass holders who want to crew and do not have a specified skipper are also welcome. Please also sign up as "skills checked crew". A Skipper's meeting will be held at 4:15 PM on the dock and all crew should be ready to go out by 4:30 PM. We will race until approximately 7 PM. Directly following the races, please join us on the bluff for a complimentary BBQ. PBCB will supply hamburgers, cheese, hot dogs, rolls, chips, paper products/cutlery, and condiments. Please feel free to bring your own beverages and/or a side to share. Post BBQ clean up will be a group effort.
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4:15 PM - 7:00 PM
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Friday Night Friendly FLYING SCOT Races - August 28th SKIPPER
Racing is a fun and challenging way to get more out of the sport of sailing. It provides an opportunity to reinforce and build your sailing skills while becoming part of a friendly community. Fine tune your boat handling skills through friendly competition. Skills checked sailors that have purchased a RACE PASS are welcome to skipper. If you wish to bring a crew that is also a skills checked sailor they as well need to have a RACE PASS, please have the sign up individually as "skills checked crew"Registration for each week will open the Monday prior to the race.You must sign up for each individual race you would like to participate in. Skills checked pass holders who want to crew and do not have a specified skipper are also welcome. Please also sign up as "skills checked crew". A Skipper's meeting will be held at 4:15 PM on the dock and all crew should be ready to go out by 4:30 PM. We will race until approximately 7 PM. Directly following the races, please join us on the bluff for a complimentary BBQ. PBCB will supply hamburgers, cheese, hot dogs, rolls, chips, paper products/cutlery, and condiments. Please feel free to bring your own beverages and/or a side to share. Post BBQ clean up will be a group effort.
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Monday September 14, 2026
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3:00 PM - 5:30 PM
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Pleasant Bay Explorers - Pleasant Bay Explorers
Curious minds belong outside! This September, Pleasant Bay Community Boating is launching PBCB Explorers, a four-week after-school program designed for young scientists, makers, and nature enthusiasts ages 10-14.Each afternoon, participants will dive into hands-on science experiments, creative building projects, microscope investigations, outdoor exploration, and nature-inspired art and engineering activities. Whether they're examining marine life, tackling fun STEM challenges, or discovering the natural world around them, every day offers a new adventure.The program begins with staggered drop-off starting at 3:00 PM to accommodate different school dismissal times. Students will enjoy a snack and time to relax before the main program runs from 3:30–5:30 PM.Program Details
Dates: September 8 – October 2, 2026 (Monday–Friday; no program on Labor Day)
Ages: 10–14
Drop-off: Begins at 3:00 PM
Program: 3:30–5:30 PM
Cost: $900 per student for the full four-week session
Discounts: 15% sibling discount available, plus scholarships for eligible families. Please contact Registrar Ellen (info@pbcb.cc) if you'd like to apply for a scholarship.
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3:30 PM - 4:30 PM
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Rewilding Sipson Island - a Native Plant Walk & Solar-powered Pontoon Boat Ride - Plant Walk and Talk on Sipson Island - Monday Sept 14th - 3:30 - 5:30 PM
Join two members of the Sipson Island Land Management Committee for a “walk and talk”. Louise and Gary will point out the native flora and describe how volunteers and staff from Wilkinson Environmental Design have worked to creative natural native plant communities by removing invasive species and restoring the native plants on 22 acres of Sipson Island in the middle of Pleasant Bay. Attendees will be brought out to Sipson on the PBCB floating classroom and we will walk the entire island upland area along wide trails. Please dress appropriately as there are ticks and weather can be variable – even on different sides of the island.About Louise Wasley: Louise has been an avid gardener since she was young. She owned a fine gardening company based in Chatham for many years and completed the Master Gardener program in 2014. She continues to volunteer and take courses. She has been working with Sipson Island Trust and the Land Management Committee since 2023. Throughout the removal of the invasives, SIT has worked diligently to restore the disturbed areas with native plantings.About Gary Bowden: Gary has been working with Sipson Island Trust and its Land Management Committee since 2022, just as the Trust was working to bring down the three homes and continue its work to rewild 22 acres of natural beauty. Gary is a resident of Orleans and been active gardener and educator since retiring and relocating from Washington DC. He completed his Master Gardener certification in 2019 and was a founding member of the Pollinator Pathway Cape Cod. He also is currently on the Board of the Orleans Conservation Trust.The tour will initiate at Pleasant Bay Community Boating located at 2287 Route 28 in Harwich. Please park in the large gravel lot and proceed to the boat house. There is limited handicap parking available at 661 Route 28, Orleans. You will travel to Sipson Island on board our electric pontoon boat " Friend'. All attendees will be required to wear a life jacket that PBCB will provide. Please dress for the elements as the weather can be quite different on the water and on the island.
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