Thursday Sep 3, 2026 Sunday Sep 6, 2026
Join our local Schooner Captains as they participate in a friendly competition putting their seamanship to the test over an ''obstacle'' course. Passengers will be given their own set of tasks to win the coveted Rum Bottle Award. Visiting schooners already arrived will join the event.
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Schooner Festival Community Day
September 3
All Day
Museums & Exhibits Open | 10 AM - 4 PM | Maritime Gloucester
A day filled with local flavor. Local captains and crew will be making the rounds throughout the community, culminating in an evening race sure to wake up the harbor!
Schooner Challenge | 5:30 – 7:30 PM
Join our local Schooner Captains as they participate in a friendly competition putting their seamanship to the test over an "obstacle" course. Passengers will be given their own set of tasks to win the coveted Rum Bottle Award. Visiting schooners already arrived will join the event. The public is invited to purchase tickets aboard participating schooners. Ticketed passengers and crew will be invited to a post challenge awards party.
Check various schooner websites for ticketing details
Schooner Festival Greet the Fleet Day
September 4
All Day
Museums & Exhibits Open | 10 AM - 4 PM | Maritime Gloucester
Schooner Deck Tours | 10 AM – 1 PM: Schooner Floats at I4C2
Public Sails | 10 AM – 5 PM
Greet the Fleet Sails | Various Departure Times
Historic Gloucester Harbor comes alive with canvas as traditional wooden vessels. With so many schooners in the harbor, here is your opportunity to be part of the action! A thrilling chance to greet visiting schooners as they come over the breakwater.
Check various schooner websites for ticketing details
Community Events
Gloucester Main Street Block Party: 6 – 10 PM
Schooner Festival Maritime Heritage Day
September 5
All Day
The festival's biggest spectator day, with 3 locations to engage with history and vessels, dozens of opportunities to get on board and view these majestic ships or sail on Gloucester Harbor. The pinnacle of the festivities revolve around Maritime Gloucester's pier with demonstrations and family fun.
Check out the day's schedule HERE
Maritime Heritage Day at Maritime Gloucester | 10 AM – 4 PM
Museums and Exhibits Open, Schooner Deck Tours
Free to the public: schooner deck tours, music, food trucks, USS Constitution 1892 Marines, crafts for all ages, skills demonstrations, community vendors, & family activities.
$30 hourly schooner sails on Schooner Ardelle!
Get your MHD schedule and details HERE
Schooner Deck Tours
Schooner Floats - I4C2, 65 Rogers St
Ocean Alliance - 32 Horton St, Rocky Neck
Thanks to generous support from our sponsors, we are again able to provide a visitor-based dockside experience that puts the public on schooners for deck tours. This is a free option for the public, but donations are always appreciated.
Public Sails | 8:30 AM – 6 PM
The public is invited to purchase tickets aboard participating schooners.
Check various schooner websites for ticketing details
Firweorks Sails | 6:30 PM – 10:30 PM
Witnessing the fireworks over historic Gloucester Harbor is a magnificent sight. Seeing it above you from the deck of a schooner is a breathtaking experience you do not want to miss. These sell out quickly, so don't delay.
Check various schooner websites for ticketing details
Community Events
Concert on Stacy Boulevard | 6:30 – 10:0 PM
Boat Parade of Lights | 7 – 9 PM
This annual event showcases a parade of local private boats and begins at dusk in the Annisquam River.
For more information: facebook.com/boatparadeoflights
Fireworks Display over the Harbor | 9:15 PM (approximate time)
Schooner Festival Greet the Fleet Day
September 6
All Day
Museums & Exhibits Open | 10 AM - 4 PM | Maritime Gloucester
Parade of Schooners | 10 AM – 11:30 AM
Schooners proceed from the Inner Harbor, past the Fisherman's Memorial on Stacy Boulevard and Stage Fort Park, to the race starting area off Eastern Point. Various non-profit and business organizations offer Parade of Schooners or Race viewing opportunities.
The public is invited to purchase tickets aboard participating schooners.
Check various schooner websites for ticketing details
Shuttle to Watch the Race | 10:30 AM – 2:30 PM
Shuttle Bus to Eastern Point Light From St. Anthony’s Church, Farrington Ave to watch the start of the Mayor's Race. Free of Charge courtesy of the Cape Ann Transportation Authority. Thank you to the Holy Family Parish for allowing us to use their parking lot.
Schooner Races | 1 PM
Start of Mayor's Races for the Esperanto Cup & the Columbia Trophy Off Eastern Point - the race course is decided the morning of the race by the Schooner Festival Committee at a meeting with the captains of the participating vessels.
The public is invited to purchase tickets aboard participating schooners.
Check various schooner websites for ticketing details
Printed courtesy of www.capeannchamber.com – Contact the Greater Cape Ann Chamber of Commerce for more information.
24 Harbor Loop, Gloucester, MA 01930 – (978) 283-1601 – info@capeannchamber.com