New Bedford’s Historic Schooner Ernestina-Morrissey Sets Sail for Gloucester Festival

The 110-foot New Bedford-based schooner Ernestina-Morrissey is among nearly two dozen vessels taking part in the 42nd annual Gloucester Schooner Festival north of Boston at Cape Ann this weekend.

A Labor Day Maritime Tradition on Cape Ann

Boston.com reported the festival is a "cherished Cape Ann tradition that began in 1985 as a rendezvous amongst schooners who gathered to race and pay homage to the International Fishermen's Cup Races of the 1920s and 1930s."

"Every Labor Day weekend, Gloucester, Massachusetts transforms into a bustling celebration of maritime history, community spirit, and – of course – majestic schooners," according to Discover Gloucester.

The Gloucester Schooner Festival is organized by Maritime Gloucester. The four-day event runs Thursday, September 3 to Sunday, September 6, 2026, bringing with it "a full slate of family-friendly events, sailing opportunities, and more." Maritime Gloucester provides a full schedule of festival events on its website as well as the 2026 Festival Program.

Historic Vessels Gathering for the 2026 Festival

The 92-foot schooner Tabor Boy from Marion, the 92-foot American Eagle and the 95-foot Harvey Gamage from Maine, and the 98-foot Dennis Sullivan from Wisconsin are among the many sailing vessels scheduled to participate in the festival.

Tabor Academy via Facebook

Parade of Sail, Deck Tours, and Public Sailing

Sunday features the Parade of Sail, a grand procession of schooners through Gloucester Harbor before participating in schooner races.

Some vessels are open throughout the weekend for public tours and others for public sails, which must be prebooked through the festival website.

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Sounds like a great way to wrap up the unofficial summer season and get ready for the holidays and winter season, which are right around the corner.

I've never experienced the Gloucester Schooner Festival, but this sounds like an addition to the "to do" list.