Tabor Boy Raises its Sails at the Gloucester Schooner Festival

Early on the morning of Friday, August 29, the Tabor Boy and her captains and crew departed Sippican Harbor, voyaging to the port of Gloucester, MA. There she would participate, for the first time, in the 41st Annual Gloucester Schooner Festival.

Over the course of the four-day festival, a dedicated group of students, alumni, friends, and trustees crewed the vessel, hosted tours, and enjoyed the camaraderie and competition of the race.

The first Gloucester Schooner Festival took place in June 1985 as a rekindling of the International Fishermen’s Races of the 1920s. Today it features races for small, medium, and large schooners with the large vessels competing for the historic “Esperanto Cup,” the original cup claimed by the crew of the schooner Esperanto upon winning the first International Fishermen’s Race in Halifax, Nova Scotia in October 1920.

Tabor Boy Captain Jay Amster was thrilled to not only participate in the race, but also at the chance to interact with other schooner crews and members of the general public who came to view the participating vessels. “We welcomed more than 650 visitors aboard for tours. Most were members of the public, but we were also thrilled to meet and greet alumni who had sailed with Captain Glaeser as far back as 1957 and 1981,” he says.

Race day, Sunday, brought more alumni and friends aboard who had volunteered to crew for the day. On her first showing, and as the only vessel with a student crew, the Tabor Boy placed third amongst other large schooners such as the Adventure, the American Eagle, and the Denis Sullivan.

“Although the wind was light, it was a fantastic day on the water with 24 hands on deck, smiles, and shared stories all around,” remarks Captain Amster.

The Tabor Boy’s time at the Gloucester Schooner Festival was more than just a great sail — it was a chance to connect our students and alumni with local maritime history, to display the life-long skills honed at the School by the Sea, and to be part of a vibrant sailing community. With her sails full and crew proud, the Tabor Boy continues to honor the enduring spirit of a nautical education, one voyage at a time.