39th Annual Gloucester Schooner Festival Schedule of Events

Visit the Schooner Festival event webpage for the most up-to-date schedule of events.

THURSDAY, AUGUST 31st

5:30 pm – 7:30 pm

SCHOONER CHALLENGE – GLOUCESTER HARBOR

Join 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 that have already arrived will join the event. The public is invited to purchase tickets aboard participating schooners.

Check various schooner websites for ticketing details.

7:00 pm

HARBOR LOOP SUMMER CONCERT SERIES – HARBOR LOOP

John Raymond Jerome  & Groove Therapy perform a free concert at Harbor Loop. 

FRIDAY, SEPTEMBER 1st

All Day

ARRIVAL OF VISITING VESSELS – GLOUCESTER HARBOR

Throughout the day, visiting vessels will be arriving into Gloucester Harbor. View them under sail as the arrive, anywhere along Gloucester Harbor.

10:00 – 4:00pm

MARITIME GLOUCESTER OPEN – 23 HARBOR LOOP

6:00 pm-10:00 pm

DOWNTOWN GLOUCESTER BLOCK PARTY – MAIN STREET

Celebrate the Schooner Festival with a street party on Gloucester’s Main Street. A fun night for all ages with live entertainment, al fresco dining, children’s activities and fun street performances!​

SATURDAY, SEPTEMBER 2nd

All Day

SCHOONER VIEWING & DECK TOURS THREE LOCATIONS:

Maritime Gloucester- 23 Harbor Loop

Schooner Floats – I4C2, 65 Rogers St

Ocean Alliance – 32 Horton St, Rocky Neck

Thanks to generous support from sponsors, Gloucester Schooner Festival is 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. Donations are always appreciated.

9:30 am

INTERNATIONAL DORY RACES

The International Dory Races, an annual tradition, are best viewed at Solomon Jacobs Park.

10:00 – 4:00pm

MARITIME GLOUCESTER HERITAGE DAY  – 23 HARBOR LOOP

Free to the public:

Schooner deck tours, crafts for all ages, skilled demonstrations & family activities. Plus, Maritime Gloucester’s exhibits and aquarium will be open throughout the day for FREE! Donations graciously accepted.

Timed Admission to the New Maritime Science Education Center. Make Reservations here.

Food Trucks on site include Beefie Boys, Uncle Joey’s Cannoli, Trolley Dogs, and Eclectic Clam

$20 hourly schooner sails on Schooner Ardelle!

6:30 pm-10:00 pm

CONCERT ON STACY BOULEVARD: LIVE MUSIC AND LIGHT EFFECTS

More details available at facebook.com/ConcertsOnTheBoulevard

7:00 pm

BOAT PARADE OF LIGHTS

The annual Boat Parade of Lights begins at dusk in the Annisquam River. For more information visit facebook.com/boatparadeoflights

9:15 pm

FIREWORKS DISPLAY OVER GLOUCESTER HARBOR

Following the Parade of Lights, time approximate. Best viewing is anywhere between Stage Fort Park, Stacy Boulevard, and Pavilion Beach.

SUNDAY, SEPTEMBER 3rd

10:00 am-11:00 am

PARADE OF SAIL, GLOUCESTER HARBOR

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 Sail or Race viewing.

11:00 am- 1:30 pm

SHUTTLE BUS TO EASTERN POINT LIGHT FROM EASTERN POINT GATE (EASTERN POINT @ FARRINGTON AVE) 

Watch the start of the Mayor’s Race. Free of Charge courtesy of the Cape Ann Transportation Authority.

​1:00 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. Read more about it in the 2023 Schooner Festival Program

MONDAY, SEPTEMBER 4th LABOR DAY

Rain Date As Needed- Parade of Sail and/or Races

10:00am – 4:00pm

MARITIME GLOUCESTER OPEN