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Great Schooner Race History

Each year the Maine Windjammer Association hosts one of the most exciting and renowned sailing events on the East Coast of the U.S. – The Annual Great Schooner Race. Did you know…that the very first race occurred in 1953?

Indeed! On September 9th, 1953, Schooners Stephen Taber and Alice S. Wentworth raced neck in neck across Penobscot Bay. The day afterward, the Bangor Daily News reported, “Before the largest crowd in schooner racing history the Maine Coasting Schooner Championship was copped by the Taber by a mere four seconds in the most thrilling race held here in years.”

It would be another 24 years before the next Great Schooner Race. In 1977, Captain Mike Anderson of Schooner Stephen Taber rekindled the Race, unfortunately losing to Schooner Isaac H. Evans, captained by Doug and Linda Lee. In 1979, Schooner Stephen Taber won the 3rd annual event.

Every year hence a fleet of majestic windjammers has raced from Gilkey Harbor in Islesboro, Maine down to Rockland Breakwater and the amazing spirit, energy, fun, and seamanship is the same now as it was in 1953. In 2022 the race shifts locations to both begin and end at the Rockland Breakwater. As it’s been, the race course is determined on the day of the race with weather and tides helping guide the windjammers. 

Stay in the Know

With the Maine Windjammer Association monthly newsletter, you’ll receive tips and hints from folks who have sailed as well as information about the best dining and attractions the area has to offer, special packages, windjammer history, events, and more!

Monthly Newsletter Signup


You may request a mailed packet of brochures, or you can find individual ships’ brochures under each listing on the fleet page on the Maine Windjammer Association Website.

Request a Packet Visit the MWA Fleet Page

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