Thursday, Sept 2

  • SCHOONER CHALLENGE – 6:00 to 7:30pm – Gloucester Harbor

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. Check various schooner websites for ticketing details.

Friday, Sept 3

  • All Day – The SCHOONERS ARRIVE – Gloucester Harbor with shoreside viewing

Historic Gloucester Harbor sets the scene for the arrival of over 2 dozen schooners throughout the day and. Spend the day viewing these wonderful vessels filling our harbor. Details of schooner arrival times will be provided as possible via social media.

6:00 to 10:00pm – Gloucester Block Party – Main Street, Gloucester

Cape Ann Chamber of Commerce and local businesses roll out the red carpet on Main Street for Gloucester Schooner Festival with a street party!  Shopping, food, entertainment, and fun are on the agenda all evening.

More Info

Saturday, Sept 4

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

The heart of land-based activities is Maritime Heritage Day! Maritime Gloucester opens its campus for a day of maritime heritage, live demonstrations, schooner sails, family fun, and food. Plan your day at Maritime Gloucester to be part of this historic year. See the full Maritime Heritage Day schedule

  • International Dory Committee Exhibition – 9:00 to 11:00am – Maritime Gloucester, 23 Harbor Loop –


We are excited to have the International Dory Race Committee be part of our 37th Annual Gloucester Schooner Festival in 2021. As we celebrate the 101st anniversary of the International Fisherman’s Race, we honor the heritage of the International Dory Races that coincided with the IFR since 1923.  At 9:00am, the committee will run an exhibition race from Maritime Gloucester Pier toward the historic Tarr & Wonson Paint Factory and back.  At 10:00am, visiting schooner crews will join for a second round of exhibition races. Solomon Jacobs Park will be a great viewing location.

  • Schooner Viewing and Deck Tours! – 10:00am to 4:00pm –

               THREE Locations:

  • Maritime Gloucester, 23 Harbor Loop

  • Schooner Floats – I4C2 parking lot, 65 Rogers St

  • *NEW THIS YEAR!* Ocean Alliance – 32 Horton Street, Rocky Neck

Schooner Map

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.  Public viewing will take place at Maritime Gloucester’s pier and at I4C2. This is a free option for the public, but donations for Gloucester Schooner Festival are appreciated to support this experience.

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


For the first time in over 50 years, the Gertrude L. Thebaud Pennant will be displayed live at Maritime Gloucester’s Gorton’s Seafoods Gallery. This 25ft by 11ft pennant was proudly flown on the Gertrude L. Thebaud and is a site to behold in pure scale.  After a small amount of work, we are once more able to hang this priceless piece of history for a limited time for public viewing.

  • Schooner Tour by Water – SOLD OUT – 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.  This is a fun way for groups to experience the Gloucester Schooner Festival.

  • 6:30 to 10:30pm – Concert on Stacy Boulevard

Live music and light effects light up the night overlooking the harbor on Stacy Boulevard.

More Info

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

Open to all who wish to decorate their boat and enter, this is a fantastic visual display starting in the Annisquam River and ending in the Smith’s Cove area of the harbor

More Info

  • 9:15 – FIREWORKS!

The night sky lights up with the annual fireworks display over Stage Fort Park.  Get on a schooner charter, watch from your boat, or enjoy from nearly anywhere in the city, this spectacle is a great way to enjoy Schooner Festival.

More Info

Sunday, Sept 5

  • Parade of Sail – 10:00am to 12:00pm – Gloucester Harbor, Stacey 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.  On the Boulevard, our Festival Chair Daisy Nell Collinson, Michael Costello, and Maritime Gloucester Historian Justin Demetri will provide live commentary. Schooners proceed from the Inner Harbor, past the Fisherman’s Memorial on Stacy Boulevard, to the race starting area off Eastern Point.

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

Catch the CATA shuttle from Eastern Point Gate (Eastern Point Boulevard at Farrington Ave) to watch the start of the Mayor’s Race. Free of charge, courtesy of Cape Ann Transportation Authority

More Info

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

The Premier Event – The Mayor’s Races!  This year’s schooners match up in small, medium, and large categories for a reach-reach competition viewing for the Esperanto Cup, The Ned Cameron Trophy, and The Betty Ramsey Award.

Monday, Sept 6 – Labor Day​

Rain Date for Heritage Day or Race. Maritime Gloucester open from 10 to 4pm

Schooner Challenge aboard the Thomas Lannon with Redbird, Thomas Story, and Ardelle

Leave a Reply