History of Maine’s Great Schooner Race

Schooner Alice S. Wentworth Circa 1938

Schooner Alice S. Wentworth Circa 1938

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. This year The Great Schooner Race will mark its 44th event. But 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.”

One particular passenger, Mr. Victor S. Bryant, who was aboard Alice S. Wentworth, wrote a stunning report about the race as he saw it. We were lucky enough to come across the original 1953 document and we typed up an easier-to-read version as well. We think Mr. Bryant most excellently captured the thrill, energy, and passion of windjammer sailing. And we just love his description of his invitation to visit to his friends, Bess and Phil. It is worth the read.

1930's Photo of Schooner Stephen Taber Hauling Lumber

1930’s Photo of Schooner Stephen Taber Hauling Lumber

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.  If you happen to sail aboard any of the vessels in the Great Schooner Race, and you feel inspired by the words of Victor S. Bryant, we would love to hear your racing story and, if you like, share your experience with others.