Gloucester Schooner Festival

September 1 –  5, 2022 | Labor Day Weekend

38th Annual Gloucester Schooner Festival

 Gloucester Schooner Festival is back! The schooners return to Gloucester in late summer to celebrate the annual Gloucester Schooner Festival. Maritime Gloucester will welcome more than 20 schooners to its recently rebuilt Harriet Webster Pier.

The weekend offers a wide range of sights and sounds. Taking place in the harbor and nearby waters of America’s oldest seaport, the Gloucester Schooner Festival honors the major role the fishing schooner – invented here in 1713 – has played in the heritage of Gloucester and the eastern seaboard. Old and new, large and small, a variety of schooners will visit Gloucester Harbor throughout the weekend, delighting all who visit. Gloucester’s beautiful harbor, acclaimed by explorer Samuel de Champlain as “Le Beauport” is the backdrop for a unique mix of modern day and traditional vessels from the age of sail. A spectacular highlight of the Gloucester Schooner Festival is the Parade of Sail on Sunday morning as participating schooners make their way through the harbor and past the breakwater, to the Mayor’s Race starting area off Eastern Point.

Visitor Information

Plan your Schooner Festival weekend and make it the best possible experience in our coastal city with Discover Gloucester as your go-to resource. Browse  for all of the info you need to STAY, DINE, and PLAY.

Gloucester Schooner Festival | Maritime Gloucester

Visit Gloucester Schooner Festival website for all the history of this maritime sailing event, the tradition, and schedule information for the weekend’s events.

Stay Tuned….for the 2022 Schooner Festival Schedule


List of Schooners


Adventure, Gloucester, MA
American Eagle, Rockland, ME
Columbia, Panama City, FL
Roseway, Boston, MA


Alert, Bailey Island, ME
Ardelle, Gloucester, MA
Fame, Salem, MA
Fritha, Fairhaven, MA
Thomas E. Lannon, Gloucester, MA
Tree of Life, Newport, RI
Tyrone, formerly Chatham, MA
When and If, Key West, FL

Festival of Events


Bald Eagle, Gloucester, MA
Calabash, Vineyard Haven, MA
Eileen Marie, Boston, MA
Green Dragon, Gloucester, MA
Istar, Provincetown, MA
Lewis H Story, Essex, MA
Malabar II, Vineyard Haven, MA
Redbird, Essex, MA
Renegade, Branford, CT
Strombus, Gloucester, MA
Sycamore, Wicasset, ME

Festival of Events

Festival of Events


  • Schooner Challenge | 6:00 pm – 7:30 pm | Gloucester Harbor

Festival of Events


  • Schooners Arrive | All Day | Gloucester Harbor with shoreside viewing


Maritime Heritage Day | 10:00 am – 4:00pm | Maritime Gloucester, 23 Harbor Loop

International Dory Committee Exhibition | 9:00 am – 11:00 am | Maritime Gloucester, 23 Harbor Loop *NEW THIS YEAR!*

Schooner Viewing and Deck Tours! | 10:00 am – 4:00 pm | THREE Locations: Maritime Gloucester, 23 Harbor Loop; Schooner Floats – I4C2 parking lot, 65 Rogers St; Ocean Alliance – 32 Horton Street, Rocky Neck

FIREWORKS! | 9:15 pm


Parade of Sail | 10:00 am – 12:00 pm | Gloucester Harbor, Stacey Boulevard and Eastern Point viewing

Shuttle Bus to Eastern Point Light | 11:00 am – 1:30 pm

Mayor’s Cup Race | 1:00 pm – 4:00 pm | Massachusetts Bay off Gloucester


Gertrude L. Thebaud Pennant Viewing | 10:00am to 4:00pm | Maritime Gloucester, 23 Harbor Loop | *NEW THIS YEAR ONLY!*

Schooner Tour by Water | times TBD (check back!) | Gloucester Harbor Tours, Solomon Jacobs Park

Concert on Stacy Boulevard | 6:30 to 10:30pm

Boat Parade of Lights | 7:00 to 9:30pm | Annisquam River and Inner Harbor

FIREWORKS! | 9:00pm


Rain Date for Heritage Day or Race.

Maritime Gloucester open from 10:00 am – 4:00 pm

Related Articles & Fun Facts

Original Pennant of the GERTRUDE L. THEBAUD 

The Gloucester Schooner Festival, in tandem with Maritime Gloucester is proud to announce the display of the original pennant of the Essex-built racing fisherman GERTRUDE L. THEBAUD.

This roughly 90-year old linen pennant was originally given to John McPhee, the “skipper” of the Gloucester Sea Scouts by Captain Ben Pine before “Piney” passed in 1953.

The pennant was often displayed by the Sea Scouts during their meetings held at the old Gloucester Fishermen’s Institute on Duncan Street.

McPhee passed the pennant on to the late former assistant Gloucester Harbormaster and Sea Scout, John “Jack” Carrancho. The pennant was then given to fellow Sea Scout Geno Mondello, a founding member of Maritime Gloucester and master of the Dory Shop located in the former Burnham Brothers Mill Building.

Roy Downs, sailmaker from Rockport, MA revived the long dormant pennant in 2021, after some 50 years of storage. Downs was in awe of the stitching of the letters, clearly a work of art that could only have been done by a clever hand.

The tiny stitches and attention to detail, he remarked, saved the original linen cloth from breaking down. A virtual miracle considering that the pennant hung from the top of a famously fast sailing vessel — none other than “galloping Gertie” herself!

A big “Thank You” goes out to Geno Mondello for the loan of this important “thread” of Gloucester history.

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