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More than 20 schooners from up and down the eastern seaboard will gather off Cape Ann this Labor Day weekend as part of the 39th Annual Gloucester Schooner Festival. From Thursday, August 31 to Sunday, September 3, schooners will sail and race through the waters of Gloucester Harbor, take passengers on thrilling sails, and allow visitors to explore their decks.

The festival kicks off on Thursday, with the Schooner Challenge, in which captains are challenged to navigate a course in the harbor – festival attendees who want to see the action close up can buy tickets to sail aboard participating ships. Ships will continue to arrive throughout Friday, with several offering public sails and charter opportunities throughout the afternoon.

Photograph courtesy of Maritime Gloucester

Saturday begins with dory races, followed by the Maritime Gloucester Heritage Day, a full day of schooner deck tours, crafts, skilled demonstrations, family activities, and food trucks. visitors will also be able to explore the Maritime Gloucester museum and aquarium for free. The day ends with the Boat Parade of Lights and fireworks over Gloucester Harbor.

On Sunday, the schooners parade from the inner harbor out to Gloucester’s Eastern Point, the starting line for the Mayor’s Races, which kick off at 1 p.m.

For a complete schedule of the event-packed weekend, visit

The festival began with the goal of celebrating Gloucester’s deep fishing and maritime heritage. Schooners are sailing ships with two or more masts, in which the mast closer to the front of the vessel is shorter than any behind it. They were developed in or around Gloucester in the early 1700s, specifically for a growing fishing industry that needed ships that could hold more fish and arrive at fishing grounds more quickly.

Since its inception, the Gloucester Schooner Festival, put on by local educational organization Maritime Gloucester, has evolved into something of a pilgrimage for schooner captains. Drawing thousands each year, the festival has become a beloved Labor Day weekend tradition.