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2019 & 2020 Events & Gatherings of the Fleet

Rockland, ME – Combine a cruise on board a historic windjammer with Maine Windjammer Association events and gatherings of the fleet. The Maine Windjammer Association has scheduled two years of events to make planning easy.

Monday, June 10, 2019/June 8, 2020 – Schooner Gam

Always celebrated on the second Monday in June, kick off the summer season with a windjammer gathering of the entire fleet. Gam is a nautical term for a friendly gathering at sea, and that’s exactly what this is! Relive the age of sail during this quiet rendezvous of more than a dozen 19th-century-style sailing ships. Location is determined by the weather of the day! Live music, traditional grog toast and festivities. Fleet Raft-Up!

Wednesday, June 26, 2019 (week of)/ June 21-27, 2020 – Windjammer Days

Windjammers from throughout Maine, including some members of the Maine Windjammer Association, gather in Boothbay Harbor for a week of fun and festivities during the last week in June. The highlight is a grand sail parade on the Wednesday of the Windjammer Days week, through picturesque Boothbay Harbor. Shoreside activities include music, races and fireworks.

Friday, July 5, 2019/July 3, 2020 – Great Schooner Race

Maine’s tall ship fleet gathers in Gilkey Harbor off Islesboro for an exciting race from Islesboro to Rockland, followed by a festive Awards Ceremony/dessert buffet with live music. 2019 marks the 43rd anniversary of the Great Schooner Race, North America’s largest annual gathering of traditional tall ships. Expect 20 historic schooners and day sailors to compete in multiple classes. Pre-Race festivities include zany small boat races where crews and guests compete in wild costume on the water. Spend the week cruising and racing. You might even get a chance to be at the wheel as your vessel crosses the finish line and help your captain win the coveted “Eat My Wake” banner. Visit for info and video.

Friday, July 12, 2019/July 10, 2020

Each July, on the second Friday the entire windjammer fleet participates in an afternoon Parade of Sail past the mile-long Rockland Breakwater, providing stunning, close-up views of Maine’s fleet of tall ships. Enjoy narration from windjammer experts and local legends.

Aug. 30 – Aug. 31, 2019/September 4-5, 2020 – Camden Windjammer Festival

The fleet gathers in picturesque Camden Harbor for festivities reminiscent of the days when hundreds of coastal schooners lined the waterfront. Festivities include a parade of sail, flag-raising ceremonies, tours of the windjammers, live music, Schooner Talent Show and fireworks. This is a great way to enjoy days of sailing capped off with the chance to take part in one of Maine’s biggest windjammer festivals.

Tuesday, September 10, 2019/September 15, 2020 – WoodenBoat Sail-In (3:00 – 5:30pm)

The fall gathering of the fleet takes place in Brooklin, Maine, headquarters of WoodenBoat Magazine and WoodenBoat School. In 2019, this event celebrates a 33-year legacy. Dine on mussels cooked over an open fire, plus fresh cider, and additional refreshments. A highlight is the live music performed by local steel drum band, Flash in the Pans and/or windjammer captains. A harbor full of historic schooners at sunset makes for great photo opportunities.

Each of the Maine Windjammer Association vessels schedules cruises that include these events. In addition to these gatherings of the fleet, enjoy a scenic cruise offering starry nights, wildlife watching, lobster bakes on the beach and of course the peaceful rhythm of the sea on your cruise.

For more information on the Maine Windjammer Fleet, and to access the cruise search tool or request a packet of member brochures, visit

Category: Press Releases

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