Gloucester Schooner Festival Schedule of Events

For More info- https://www.maritimegloucester.org/sf-visitor-info

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. 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

  • 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 5 – Labor Day

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

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