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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
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.
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
Maritime Gloucester, 23 Harbor Loop
Schooner Floats – I4C2 parking lot, 65 Rogers St
Ocean Alliance – 32 Horton Street, Rocky Neck
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