Gloucester Schooner Festival

About This Event

Picture this: magnificent tall ships with billowing sails gliding into Gloucester Harbor while you watch from the cockpit during your approach. The Gloucester Schooner Festival transforms this historic fishing port into a maritime wonderland every Labor Day weekend. These aren't just pretty boats to admire from afar – you can actually board these beauties for deck tours and feel the salt spray as they compete in the thrilling Mayor's Cup Races. What makes this festival absolutely irresistible is the combination of maritime history and Gloucester's legendary seafood scene. While the schooners steal the show on the water, you'll be feasting on some of the freshest lobster, scallops, and fish you've ever tasted right in the heart of New England's most storied fishing community. After 40+ years, this festival has perfected the art of celebrating both sailing heritage and coastal cuisine. Trust me, watching these graceful vessels race while you're savoring a lobster roll is pure magic.