Gloucester Schooner Festival is a weekend full of fun and exciting events across the entire city. The Gloucester Schooner Festival Committee is pleased to partner with many other local entities to create these fun events for our visitors and our community. Not all of the items below are run or offered by the Gloucester Schooner Festival, but are listed here to provide information to visitors. Information on shaded events or services should contact the organizers of those events for full details. For more information, please visit our tourism partner, DISCOVERGLOUCESTER.COM
2025 Schedule Subject to Change- Check Back Often!
2025 Schedule of Events
WEDNESDAY
Aug
27
2025
WELCOME TO
GLOUCESTER!
10:00am
to 4:00pm
MARITIME GLOUCESTER
Museums and Exhibits Open
3:00pm
to 5:00pm
MARITIME GLOUCESTER
First Look at the 2025 Gloucester Schooner Festival Merch. This is your first chance to get your hands on this year's line. We've got t-shirts, v-necks, crew necks, long sleeve, hats, water bottles and even a comfy blanket!
Unfortunately the concert at The Cut was canceled due to reasons beyond our control. We apologize for any inconvenience. Please reach out to The Cut for refunds.
THURSDAY
Aug
28
2025
COMMUNITY
DAY
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!
On Land:
10:00am
to 4:00pm
12:00pm
to 1:00pm
3:00pm
to 4:00pm
MARITIME GLOUCESTER
Museums and Exhibits Open
MARITIME KIDS CRAFT AND CREATE
Kids Heritage Craft PopUp in the MG Classroom
Join our Historian Justin Demetri and local and visiting Schooner Captains and learn more about them and why they do what they do! Apple Cider & Cider Donuts provided by Russell Orchards RSVP Here
Come Sailing:
5:30pm
to 7:30pm
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
Community/Partner Events:
4:00pm
to 7:00pm
Culture Splash
check out more info at DiscoverGloucester.com
7:00pm
to 9:30pm
Harbor Loop Concert Series
check out more info at DiscoverGloucester.com
FRIDAY
Aug
29
2025
GREET THE FLEET
DAY
As visiting sails cross the breakwater, Gloucester Harbor comes alive again, harkening back to the golden days of our Fishing Fleet under sail. This day signals the annual pilgrimage of historic wooden vessels returning to Gloucester Harbor.
On Land:
10:00am
to 3:00pm
MARITIME GLOUCESTER
Museums and Exhibits Open
Schooner Deck tours
Schooner Floats at I4C2
10am-1pm
Come Sailing:
10:00am
to 2:00pm
The public is invited to purchase tickets aboard participating schooners.
Check various schooner websites for ticketing details
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/Partner Events:
7:00pm
to 10:00pm
Chamber of Commerce Block Party
check out more info Here
SATURDAY
Aug
30
2025
MARITIME HERITAGE 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
On Land:
10:00am
to 4:00pm
MARITIME HERITAGE DAY AT MARITIME GLOUCESTER
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.
$25 hourly schooner sails on Schooner Ardelle!
Get your MHD schedule and details HERE
12:00pm
to 4:00pm
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.
Come Sailing:
10:00am
& 11:00am
Step aboard the Cape Ann Harbor Tours shuttle and set off for a 1 hour tour with Michael O’Leary—local guide and singer—as your host. Cruise the harbor for an unforgettable up-close look at Gloucester’s visiting and homeport vessels, all while hearing stories, songs, and history that bring the waterfront to life.
8:30am
to 6:00pm
The public is invited to purchase tickets aboard participating schooners.
Check various schooner websites for ticketing details
6:30pm
to 10:30pm*
FIREWORKS SAILS
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
*sail times approximate, please check individual vessel tickets
Community/Partner Events:
6:30pm
to 10:00pm
Concert on Stacy Boulevard
Live Music and light effects
More details at facebook.com/ConcertsOnTheBoulevard
7:00pm
to 9:00pm
Boat Parade of Lights
This annual event showcases a parade of local private boats and begins at dusk in the Annisquam River.
For more information: facebook.com/boatparadeoflights
9:15pm
Fireworks Display over the Harbor
time is approximate
SUNDAY
Aug
31
2025
RACE DAY!
The capping day of events culminates in the gorgeous spectacle of the Parade of Schooners and the Offshore race for the Mayors' Cup.
Come Sailing:
On Land:
10:00am
to 4:00pm
MARITIME GLOUCESTER
Museums and Exhibits Open
10:00am
to 11:30am
Parade of Schooners
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.
10:30am
to 2:30pm
Shuttle to Watch Races
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.
1:00 pm
Schooner Races
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.
9:00am
to 12:00pm
PARADE OF SCHOONERS
The public is invited to purchase tickets aboard participating schooners.
Check various schooner websites for ticketing details
various departure times, check schooner schedule
MAYOR'S CUP RACE
The Mayor's Cup, Esperanto Trophy, and many other awards are up for grabs in this thrilling off-shore race. The race course positions are 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
Visitor Information
To plan your visit to Gloucester, you need to Discover Gloucester! Our local Destination Marketing Organization has all the info you need to make your Schooner Festival weekend the best possible experience!
Check out Discover Gloucester to learn more on how to stay, play, dine, and experience everything Gloucester has to offer!
2025 Dates: Wednesday, Aug 27th - Sunday, Aug 31st
Contact Us At: Schooner@MaritimeGloucester.org
© 2025 Maritime Gloucester®. All Rights Reserved.Gloucester Schooner Festival® is a registered trademark of Gloucester Maritime Heritage Center.