Gloucester Schooner Festival

August 31 – September 4, 2023 | Labor Day Weekend

Welcome to the 39th annual Gloucester Schooner Festival!

This year, the festival starts Thursday, August 31st, 2023 and concludes with the schooner race on Sunday, September 3rd, 2023.  This capstone to the summer is steeped in history and jam-packed with events and opportunities to get up-close and personal with these beautiful ships. The GSF has become a Labor Day weekend tradition for thousands of people every year and we hope you will join in the festivities!

The Gloucester Schooner Festival is an event put on by Maritime Gloucester and has become a community wide celebration of the age of sail in Gloucester Harbor. Every year schooners from all over travel to Gloucester to race and to show off their beauty and grace both under sail and as a dock-side attraction. This website is designed to offer all the information you will need to plan an exciting weekend on and off the water. 

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.

Over the years, the Gloucester Schooner Festival has become an internationally recognized maritime and sailing event. Here are a handful of the more than 20 schooners you can expect to see including where they will be docked along the piers in Gloucester Harbor. There will be ample opportunities to tour the decks, set sail, or watch as they join in the Parade of Sail. 

    • Ernestina Morrisey, Massachusetts Flagship at the Maritime Gloucester Pier
    • Ardelle at the Maritime Gloucester Pier
    • Thomas E. Lannon at Seven Seas Wharf near I4C2
    • Bald Eagle Mooring 
    • Isabella at Maritime Gloucester Pier
    • Adventure at the I4C2 Schooner Docks
    • Denis Sullivan at the I4C2 Schooner Docks
    • Alert at the I4C2 Schooner Docks
    • Redbird Mooring

Visitors can get a personal and up-close experience with these magnificent vessels however they choose. Learn the history of the schooner with a deck tour aboard several of the vessels, or buy a ticket and get aboard for the thrill of open sail aboard these fantastic fishing schooners in historic Gloucester Harbor.

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

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

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

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

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.


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. 


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!


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

7:00 pm

Boat Parade of Lights

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


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.


10:00 am-4:00 pm

Maritime Gloucester Open – 23 Harbor Loop

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


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

10:00am – 4:00pm

Maritime Gloucester Open

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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