Classic Festival / Race · Updated August 28, 2026
Listings of public events. Master Mariner Directory is not affiliated with, endorsed by, or involved in organizing this event. Information is compiled from publicly available sources; confirm dates and entry details with the organizer directly.
- Dates
- September 3–6, 2026
- Venue
- Gloucester Harbor
- Host
- Maritime Gloucester
- Address
- 23 Harbor Loop, Gloucester, MA 01930
Getting there
Maritime Gloucester and Gloucester Harbor sit on Harbor Loop at the working waterfront of America’s oldest seaport. From Route 128 north, follow signs to downtown Gloucester and the harbor; shore-side festival events and schooner viewing concentrate along the waterfront.
About the event
The 42nd annual festival brings traditional schooners to Gloucester Harbor for parades of sail, deck tours, and the Mayor’s Cup Races over Labor Day weekend. Maritime Gloucester hosts the celebration that has drawn crowds for more than four decades.