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Friday September 18, 2026
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9:00 AM - 12:00 PM
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2026 Catboat Cruises - Catboat Cruise - Friday 9/18 - 9 AM to noon - CREW
Join us on select dates as we cruise the bay. Open to both skills checked skippers and those who would like to be crew members. Cruises are a separate program from boat rentals and Pleasant Bay Passes are not eligible to be used for payment .
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9:00 AM - 12:00 PM
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2026 Catboat Cruises - Catboat Cruise - Friday 9/18 - 9 AM to noon - SKIPPER
Join us on select dates as we cruise the bay. Open to both skills checked skippers and those who would like to be crew members. Cruises are a separate program from boat rentals and Pleasant Bay Passes are not eligible to be used for payment .
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2:00 PM - 5:00 PM
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Pleasant Bay Pass Holder Rentals - 9/14 - 9/18: Afternoon Catboat Rentals
Notices:- September rental slots are now live, weekdays through 9/25. We will keep everybody posted re: whether we're able to extend the season further, or whether we will end up having to pull the boats for a storm. - Please note that our rental hours have shifted to 1 session from 2 - 5 PM, starting on Monday 8/31.- We will be closed for rentals on the following dates: 9/12 and 9/13 for the Sandpiper Invitational, and 9/19 for Celebrate our Waters.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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2:00 PM - 5:00 PM
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Pleasant Bay Pass Holder Rentals - 9/14 - 9/18: Afternoon Flying Scot Rentals
Notices:- September rental slots are now live, weekdays through 9/25. We will keep everybody posted re: whether we're able to extend the season further, or whether we will end up having to pull the boats for a storm. - Please note that our rental hours have shifted to 1 session from 2 - 5 PM, starting on Monday 8/31.- We will be closed for rentals on the following dates: 9/12 and 9/13 for the Sandpiper Invitational, and 9/19 for Celebrate our Waters.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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Saturday September 19, 2026
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9:00 AM - 10:00 AM
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Celebrate our Waters on Pleasant Bay - Celebrate our Waters Sailing - Saturday September 19th at 9:00am
Registration will open on September 1st at 8 AM. In the meantime, feel free to create an account in our system, so you'll be able to quickly and easily register. Each person in your party should be added to your account and registered. (If you have 4 people in your family, make sure all 4 names are booked.)Join us on Saturday September 19th, 2026, as we help The Orleans Pond Coalition Celebrate our Waters. Pleasant Bay Community Boating will be offering sailing experiences on Pleasant Bay--one hour sails with an experienced skipper. Pre-registration is required. Pleasant Bay Community Boating is located at 2287 Rt 28 on the Orleans/Brewster/Harwich line. Please park in the large gravel lot and proceed over the hill to the boathouse - follow the rope walk from the parking lot. All minors must be accompanied by a parent or guardian. All participants are required to wear a life jacket, PBCB will have plenty on hand. This is a free event courtesy of PBCB, but donations are always welcomed to support our mission of making boating and marine education along with environmental stewardship of Pleasant Bay possible.Pleasant Bay Community Boating (etapestry.com)
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10:30 AM - 11:30 AM
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Celebrate our Waters on Pleasant Bay - Celebrate our Waters Sailing - Saturday September 19th at 10:30am
Registration will open on September 1st at 8 AM. In the meantime, feel free to create an account in our system, so you'll be able to quickly and easily register. Each person in your party should be added to your account and registered. (If you have 4 people in your family, make sure all 4 names are booked.)Join us on Saturday September 19th, 2026, as we help The Orleans Pond Coalition Celebrate our Waters. Pleasant Bay Community Boating will be offering sailing experiences on Pleasant Bay--one hour sails with an experienced skipper. Pre-registration is required. Pleasant Bay Community Boating is located at 2287 Rt 28 on the Orleans/Brewster/Harwich line. Please park in the large gravel lot and proceed over the hill to the boathouse - follow the rope walk from the parking lot. All minors must be accompanied by a parent or guardian. All participants are required to wear a life jacket, PBCB will have plenty on hand. This is a free event courtesy of PBCB, but donations are always welcomed to support our mission of making boating and marine education along with environmental stewardship of Pleasant Bay possible.Pleasant Bay Community Boating (etapestry.com)
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12:00 PM - 1:00 PM
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Celebrate our Waters on Pleasant Bay - Celebrate our Waters Sailing - Saturday September 19th at 1200pm
Registration will open on September 1st at 8 AM. In the meantime, feel free to create an account in our system, so you'll be able to quickly and easily register. Each person in your party should be added to your account and registered. (If you have 4 people in your family, make sure all 4 names are booked.)Join us on Saturday September 19th, 2026, as we help The Orleans Pond Coalition Celebrate our Waters. Pleasant Bay Community Boating will be offering sailing experiences on Pleasant Bay--one hour sails with an experienced skipper. Pre-registration is required. Pleasant Bay Community Boating is located at 2287 Rt 28 on the Orleans/Brewster/Harwich line. Please park in the large gravel lot and proceed over the hill to the boathouse - follow the rope walk from the parking lot. All minors must be accompanied by a parent or guardian. All participants are required to wear a life jacket, PBCB will have plenty on hand. This is a free event courtesy of PBCB, but donations are always welcomed to support our mission of making boating and marine education along with environmental stewardship of Pleasant Bay possible.Pleasant Bay Community Boating (etapestry.com)
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Monday September 21, 2026
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2:00 PM - 4:00 PM
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"Simply Sail" Private Lessons - Simply Sail with Charlie - Monday September 21st - 2 - 4 PM
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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2:00 PM - 5:00 PM
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Pleasant Bay Pass Holder Rentals - 9/21 - 9/25: Afternoon Catboat Rentals
Notices:- September rental slots are now live, weekdays through 9/25. We will keep everybody posted re: whether we're able to extend the season further, or whether we will end up having to pull the boats for a storm. - Please note that our rental hours have shifted to 1 session from 2 - 5 PM, starting on Monday 8/31.- We will be closed for rentals on the following dates: 9/12 and 9/13 for the Sandpiper Invitational, and 9/19 for Celebrate our Waters.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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2:00 PM - 5:00 PM
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Pleasant Bay Pass Holder Rentals - 9/21 - 9/25: Afternoon Flying Scot Rentals
Notices:- September rental slots are now live, weekdays through 9/25. We will keep everybody posted re: whether we're able to extend the season further, or whether we will end up having to pull the boats for a storm. - Please note that our rental hours have shifted to 1 session from 2 - 5 PM, starting on Monday 8/31.- We will be closed for rentals on the following dates: 9/12 and 9/13 for the Sandpiper Invitational, and 9/19 for Celebrate our Waters.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 September 22, 2026
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2:00 PM - 5:00 PM
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Pleasant Bay Pass Holder Rentals - 9/21 - 9/25: Afternoon Catboat Rentals
Notices:- September rental slots are now live, weekdays through 9/25. We will keep everybody posted re: whether we're able to extend the season further, or whether we will end up having to pull the boats for a storm. - Please note that our rental hours have shifted to 1 session from 2 - 5 PM, starting on Monday 8/31.- We will be closed for rentals on the following dates: 9/12 and 9/13 for the Sandpiper Invitational, and 9/19 for Celebrate our Waters.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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2:00 PM - 5:00 PM
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Pleasant Bay Pass Holder Rentals - 9/21 - 9/25: Afternoon Flying Scot Rentals
Notices:- September rental slots are now live, weekdays through 9/25. We will keep everybody posted re: whether we're able to extend the season further, or whether we will end up having to pull the boats for a storm. - Please note that our rental hours have shifted to 1 session from 2 - 5 PM, starting on Monday 8/31.- We will be closed for rentals on the following dates: 9/12 and 9/13 for the Sandpiper Invitational, and 9/19 for Celebrate our Waters.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 September 23, 2026
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2:00 PM - 4:00 PM
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"Simply Sail" Private Lessons - Simply Sail with Charlie - Wednesday September 23rd - 2 - 4 PM
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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2:00 PM - 5:00 PM
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Pleasant Bay Pass Holder Rentals - 9/21 - 9/25: Afternoon Catboat Rentals
Notices:- September rental slots are now live, weekdays through 9/25. We will keep everybody posted re: whether we're able to extend the season further, or whether we will end up having to pull the boats for a storm. - Please note that our rental hours have shifted to 1 session from 2 - 5 PM, starting on Monday 8/31.- We will be closed for rentals on the following dates: 9/12 and 9/13 for the Sandpiper Invitational, and 9/19 for Celebrate our Waters.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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2:00 PM - 5:00 PM
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Pleasant Bay Pass Holder Rentals - 9/21 - 9/25: Afternoon Flying Scot Rentals
Notices:- September rental slots are now live, weekdays through 9/25. We will keep everybody posted re: whether we're able to extend the season further, or whether we will end up having to pull the boats for a storm. - Please note that our rental hours have shifted to 1 session from 2 - 5 PM, starting on Monday 8/31.- We will be closed for rentals on the following dates: 9/12 and 9/13 for the Sandpiper Invitational, and 9/19 for Celebrate our Waters.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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3:00 PM - 6:00 PM
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Float and Paint aboard our Floating Classroom - Float & Paint Wednesday September 23rd 3:00pm Capt. Bart/ Mate JP
Join us on September 23rd for a unique, immersive art experience on the water! Artist Gwen Leonard will lead participants through a guided lesson aboard our solar-powered floating classroom pontoon boat, the Friend. All materials and refreshments provided. Come gain some new painting skills while learning more about PBCB and Pleasant Bay. About the instructor: Gwen Leonard is an award-winning artist specializing in impressionism, with a particular focus on watercolor and oil mediums. After studying for 15 years at the prestigious Art Student League in New York City, she has honed her craft and developed a distinctive style. Gwen is also an experienced educator, teaching plein air, introductory watercolor, and paint-and-sip classes throughout Massachusetts. Her work has been showcased in numerous juried art shows, where she continues to earn recognition for her mastery of the impressionist technique and her innovative approach to the medium. Painting credit to our Adaptive Coordinator, Jeff, who will be on board!
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Thursday September 24, 2026
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2:00 PM - 5:00 PM
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Pleasant Bay Pass Holder Rentals - 9/21 - 9/25: Afternoon Catboat Rentals
Notices:- September rental slots are now live, weekdays through 9/25. We will keep everybody posted re: whether we're able to extend the season further, or whether we will end up having to pull the boats for a storm. - Please note that our rental hours have shifted to 1 session from 2 - 5 PM, starting on Monday 8/31.- We will be closed for rentals on the following dates: 9/12 and 9/13 for the Sandpiper Invitational, and 9/19 for Celebrate our Waters.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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2:00 PM - 5:00 PM
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Pleasant Bay Pass Holder Rentals - 9/21 - 9/25: Afternoon Flying Scot Rentals
Notices:- September rental slots are now live, weekdays through 9/25. We will keep everybody posted re: whether we're able to extend the season further, or whether we will end up having to pull the boats for a storm. - Please note that our rental hours have shifted to 1 session from 2 - 5 PM, starting on Monday 8/31.- We will be closed for rentals on the following dates: 9/12 and 9/13 for the Sandpiper Invitational, and 9/19 for Celebrate our Waters.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 - 5:30 PM
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Bog Walk & Talk: September 24th at 4:30 PM - Bog Walk & Talk: September 24th at 4:30 PM
Enjoy a guided tour of the Three Towns Cranberry Bog, just across the street from Pleasant Bay. Local expert Herb will talk about the history of the commercial cranberry industry, and specifically the history of this bog–which does span 3 towns. Herb will discuss cranberry growing and harvesting, as well as the bog’s flora and fauna. The guided tour will be followed by sunset refreshments in the boathouse. Space is limited, so sign up today!
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Friday September 25, 2026
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2:00 PM - 5:00 PM
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Pleasant Bay Pass Holder Rentals - 9/21 - 9/25: Afternoon Catboat Rentals
Notices:- September rental slots are now live, weekdays through 9/25. We will keep everybody posted re: whether we're able to extend the season further, or whether we will end up having to pull the boats for a storm. - Please note that our rental hours have shifted to 1 session from 2 - 5 PM, starting on Monday 8/31.- We will be closed for rentals on the following dates: 9/12 and 9/13 for the Sandpiper Invitational, and 9/19 for Celebrate our Waters.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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2:00 PM - 5:00 PM
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Pleasant Bay Pass Holder Rentals - 9/21 - 9/25: Afternoon Flying Scot Rentals
Notices:- September rental slots are now live, weekdays through 9/25. We will keep everybody posted re: whether we're able to extend the season further, or whether we will end up having to pull the boats for a storm. - Please note that our rental hours have shifted to 1 session from 2 - 5 PM, starting on Monday 8/31.- We will be closed for rentals on the following dates: 9/12 and 9/13 for the Sandpiper Invitational, and 9/19 for Celebrate our Waters.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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