Gloucester Schooner Festival

Wed Aug 27, 2025 - Sun Aug 31, 2025
- see all dates
Repeating every days through August 31, 2025.
Various times
Age: All ages
Price: Free
Invite a friend Website

The Gloucester Schooner Festival takes place in America's oldest seaport over Labor Day Weekend. Events include the annual Mayor's Cup Race, schooner tours, a concert, a boat parade of lights, and fireworks.

Local schooners engage in a friendly race on Thursday, kicking off a long weekend of festivities. Two dozen boats arrive on Friday as the city hosts a block party. Saturday features Maritime Heritage Day, full of family fun. The Parade of Sail takes place on Sunday morning, as the participating schooners make their way through the harbor and out past the breakwater, to the Mayor’s Race.

** Activity dates/times are subject to change. Please click through to the activity website to verify.