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Photo: Len Burgess

Gloucester Schooner Festival is a weekend full of fun and exciting events across the entire city. The Gloucester Schooner Festival Committee is pleased to partner with many other local entities to create these fun events for our visitors and our community. Not all of the items below are run or offered by the Gloucester Schooner Festival, but are listed here to provide information to visitors. Information on shaded events or services should contact the organizers of those events for full details.  For more information, please visit our tourism partner, DISCOVERGLOUCESTER.COM


Thursday, Sept 1

  • SCHOONER CHALLENGE - 5:30 to 7:30pm - Gloucester Harbor

Festival Schedule

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 2

  • 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.

  • 6:00 & 7:00pm - Harbor Tour of Schooner Fleet 

Join Cape Ann Harbor Tours for an evening harbor cruise of the schooner fleet. Tickets are $15 and will be sold on the boat. Boat will be located on the Coast Guard docks next to Maritime Gloucester.

Saturday, Sept 3

  • International Dory Committee Exhibition - 9:00 am - Maritime Gloucester, 23 Harbor Loop

  • Maritime Heritage Day - 10 am - 4 pm - Maritime Gloucester, 23 Harbor Loop 

The heart of the Gloucester Schooner Festival's land-based activities is Maritime Heritage Day, distributed over 3 locations in downtown Gloucester! Maritime Gloucester opens its campus for a day of maritime heritage, live demonstrations, schooner sails, family fun, and new this year our Heritage Galley food truck court! We also have schooner viewing, deck tours and community organizations at the schooner docks at 65 Rogers street and across the harbor at Ocean Alliance.  See the full Maritime Heritage Day schedule here.

  • 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

  • Ocean Alliance - 32 Horton Street, Rocky Neck

  • 6:00 & 7:00pm - Harbor Tour of Schooner Fleet 

Join Cape Ann Harbor Tours for an evening harbor cruise of the schooner fleet. Tickets are $15 and will be sold on the boat. Boat will be located on the Coast Guard docks next to Maritime Gloucester.

  • 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. Click here for details

  • 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.

Sunday, Sept 4

  • 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. NEW THIS YEAR Good Morning Gloucester will be live streaming the Parade of Sail! Now you can tune in to the commentary if you are at Stage Fort Park or watch from your computer if you aren't able to make it in person! Schooners proceed from the Inner Harbor, past the Fisherman's Memorial on Stacy Boulevard, to the race starting area off Eastern Point. Click Here for Live Stream.

  • 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. Non-residents CAN park on Farrington in the resident area and will not be ticketed but must leave when the race is over. Free of charge, courtesy of Cape Ann Transportation Authority

  • 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, The Betty Ramsey Award, and the George Nichols & Amanda Madeira Woman at the Wheel Award. 

Visitor Info

Monday, Sept 5 - Labor Day

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

Visitor Information

To plan your visit, you need to Discover Gloucester!  Our local Destination Marketing Organization has all the info you need to make your Schooner Festival weekend the best possible experience! 


Check out Discover Gloucester to learn more on how to stay, play, dine, and experience everything Gloucester has to offer!


Dates: Thursday Sept 1st - Monday Sept 5th

Contact Us At:

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The 38th Annual Gloucester Schooner Festival is made possible due to our generous sponsors:

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