The Mission of the Great Provincetown Schooner Regatta is to celebrate the role of the Great Atlantic fishing bank schooner in Provincetown’s maritime history while providing educational opportunities for residents and visitors to experience these historic vessels both in port and at sea. Additionally, we educate the public about the schooner races held off the New England coast from 1886 to 1938, and commemorate Provincetown’s 1907 Lipton Cup victory. The Regatta shares the story of Provincetown’s place in the traditional fishing industry as well as educates the younger generations about the days of Cape Cod’s past, when commerce and transportation truly ‘ran with the wind’.
We work in tandem with cultural and research institutions in Provincetown and Cape Cod to enhance and reinforce the links between our local maritime history, fishing schooners, sailing, the great resources of our region, our culture and our economy.



Located at the outermost tip of Cape Cod and well-noted for being the first landing place of the Pilgrims in 1620, Provincetown was the first great fishing port on the eastern seaboard dating back to the time of the Norsemen. Many of the leading fishing vessels that plied the waters of the Atlantic and Pacific Oceans throughout America’s early maritime history called Provincetown home. Her skippers were well known for their skill and seamanship. At the height of the commercial fishing in the 19th century, Provincetown harbored as many as 100, 90-ton Schooners and 700 vessels. The port of Provincetown was also responsible for three times the catch of any other fishing port in New England.

The first Great Provincetown Schooner Race was held in 2002. Provincetown resident Captain John Bennett had been racing his Schooner Hindu in the Gloucester Schooner Festival and was inspired to organize a schooner gathering in his homeport. Although Captain Bennett did not live to see his dream come to fruition, supported by the Provincetown community, the committee that he had formed hosted the inaugural regatta that September in his honor. All who participated in this effort were inspired by Captain Bennett’s passion for sailing, his love of historic Schooners and his philosophy that good fellowship and good times are an important part of everyone’s life.
The first event was such a success that its organizers were urged to carry on the tradition and further, to expand the event to other vessels, both historic and modern. The race became a regatta for schooners, catboats, other historic vessels and modern sailing yachts and small boats.

Photo Courtesy of Deirdre Tasha





The Challenge for the Fishermen’s Cup,
the first Schooner race of the annual Regatta, runs a course from Gloucester to Provincetown. It commemorates the Lipton Cup race of 1907 in which the Schooner Rose Dorothea of Provincetown triumphed. Sir Thomas J. Lipton, a sailing enthusiast and founder of the Lipton Tea Company, provided the trophy for this race and it was presented to Captain Marion Perry by the Mayor of Boston, John F. “Honey Fitz” Fitzpatrick, grandfather of the late Senator Edward “Ted” Kennedy. The original one-of-a-kind silver cup currently resides in the Provincetown Public Library, which also houses a half-scale replica of the Rose Dorothea, constructed by local boat builder Francis “Flyer” Santos.


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Photos by Nancy Bloom, All Rights Reserved