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38th Annual Gloucester Schooner Festival

September 1 @ 5:30 pm - September 4 @ 4:00 pm

Since 1985, the Gloucester Schooner Festival has evolved and become internationally recognized as a major maritime and sailing event. The 38th Annual Gloucester Schooner Festival is organized by the Gloucester Schooner Festival Committee and Maritime Gloucester, celebrating the history and future of maritime arts and skills.  Here is the full Labor Day weekend schedule:

Thursday, September 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, September 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

The Greater 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 you can click here to visit their website and register.

Saturday, September 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 you can click here to visit their website and register.

  • 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, September 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.

  • 11:00am 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

  • 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.

Monday, September 5 – Labor Day​

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

Details

Start:
September 1 @ 5:30 pm
End:
September 4 @ 4:00 pm
Event Categories:
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Website:
https://www.maritimegloucester.org/sf-visitor-info

Organizer

Maritime Gloucester
View Organizer Website

Venue

Gloucester Harbor
Gloucester,MA01930United States+ Google Map
View Venue Website