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.

Gloucester Schooner Festival | Maritime Gloucester

Visit the Gloucester Schooner Festival website for the history and tradition of this maritime event, and for the most up-to-date events schedule.

Do you have great photos or video footage from Schooner Festival? Send them to Discover Gloucester for a chance to be featured in our media. Click here to submit your photos and videos. You’ll also be entered in a drawing to win a Gloucester Goody Bag!

Visitor Information

Plan your Schooner Festival weekend in beautiful Gloucester: America’s Oldest Seaport. Browse for all of the info you need to STAY, DINE, and PLAY during Schooner Festival. You can use our new Plan Your Visit tool to map out your itinerary – click here to plan your weekend!

Getting Around Town

Arriving to Gloucester by Train:

Take the MBTA Commuter Rail to the Gloucester Station. Walk down to the harbor, and return using the CATA Trolley (Sat, Sun & Mon only). Find a map and schedule at:

CATA On Demand:

CATA’s On Demand ride share program is an easy way to get around town. Download the CATA On Demand app and follow the instructions for ordering a ride-share for just $2 each way. This is a great option when arriving by train or staying at one of our local hotels. Enjoy views of the Parade of Sail from Eastern Point by taking CATA to Niles Beach and transferring to the shuttle.

Parking Options:

  • Stage Fort Park – 10 minute walk from downtown Schooner sites. Click here to reserve parking.
  • Rogers Street – Metered parking available — pay at the designated kiosk or by using the Flow Bird app.
  • Stacy Boulevard – Parking is available, but limited. Be sure to double check signage for regulations.

Cape Ann Habor Tours Water Shuttle:

Visit Rocky Neck and Ocean Alliance with ease by hopping aboard the Cape Ann Harbor Tours Water Shuttle which docks downtown at the Harbormaster Building located in Harbor Loop. Get around the inner harbor easily to visit Schooner Fest sites, and enjoy views of Schooners from the water. The water shuttle is step-on, step-off and just $10 per day.

Schooner Viewing and Deck Tours

Saturday, Sept. 3| 10:00am-4:00pm

This visitor-based dockside experience is thanks to generous support from Schooner Festival sponsors. Public viewing will take place at Maritime Gloucester’s pier, Ocean Alliance, and at I4C2. This is a free option for the public, but donations for Gloucester Schooner Festival are appreciated to support this experience. Click here to learn more.

Schooner Tour by Water

Saturday, Sept. 3 | Gloucester Harbor Tours, Solomon Jacobs Park

Gloucester Harbor Tours teams up with Gloucester Schooner Festival to provide a narrated tour of the Schooners at the dock and on their moorings. This water-based tour will give ticketed customers a chance to hear about local maritime history and view these vessels from a unique perspective.

Charter a Schooner

Saturday, Sept. 4 & Sunday, Sept. 5 | See Schooner Map

Schooner Charters are available! Visit the Schooner Festival website to see the list of participating schooners, and book a charter. Schooners pictured with a yellow star are selling tickets for the public to sail aboard during The Mayor’s Races on Sunday! Click here to learn more.

Parade of Sail

Sunday, Sept. 4| 10:00am to 12:00pm |  Gloucester Harbor, Stacy Boulevard and Eastern Point viewing

The entire fleet of schooners joins together for a Parade of Sail not to be missed! Whether you get aboard a schooner or watch from the shore, this is a memorable experience for all. Prime viewing areas are Stacy Boulevard, Stage Fort Park, and Eastern Point. Click here to learn more.

Schedule of Events

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


  • Schooner Challenge | 6:00 pm – 7:30 pm | Gloucester Harbor
  • Harbor Loop Concert | 5:30-9:30pm | Harbor Loop


Schooners Arrive | All Day | Gloucester Harbor with shoreside viewing

What Time Is It, Mr. Fox? | 6:00-8:30pm | Performance at Music on Meetinghouse Green

Main Street Block Party | 6:00-10:00pm | Main Street in Gloucester


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

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

Gertrude L. Thebaud Pennant Viewing | 10:00am – 4:00pm | Maritime Gloucester, 23 Harbor Loop

Schooner Tour by Water | 10:00am – 4:00pm | Gloucester Harbor Tours, Solomon Jacobs Park

Once Upon A Whale Song Exhibit with Artist Perri Howard | 10:00am-2:00pm| Ocean Alliance, 32 Horton Street

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

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

FIREWORKS! | 9:00pmFIREWORKS! | 9:15 p


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


Rain Date for Heritage Day or Race.

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

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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