TEN FRIDAY NIGHTS. TEN GREAT OUTDOOR CONCERTS TO BENEFIT TEN OF OUR LOCAL NON-PROFITS. ONE GREAT SUMMER ON THE GREEN.

A series of free outdoor concerts on Meetinghouse Green, corner of Church and Middle St, Gloucester. The family-friendly concerts begin at 6 pm — bring folding chairs or blankets. Food vendors at every concert, and the public is invited to make free-will donations to the Cape Ann non-profit partnered with each concert.

The Goddesses
Fri · September 4, 2026 · 6:00pm

The Goddesses

Free, Donations Encouraged. · Benefits HAWC · Food by Meat & Sweet

Gloucester’s own Goddesses light up the night with an evening of classic rock ‘n roll. Dust off your best dance moves and get ready for a spectacular…

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Henri Smith and Ensemble
Fri · September 11, 2026 · 6:00pm

Henri Smith and Ensemble

Free, Donations Encouraged. · Benefits Gloucester Meetinghouse Foundation · Food by The Lobster Roller

New Orleans comes home to Cape Ann. Jazz vocalist Henri Smith — a 13th Ward native raised among the Neville Brothers and Fats Domino, a longtime WWOZ radio…

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2026 CAPE ANN CLASSIC CARS Show
Sat · September 26, 2026 · 10:00am

2026 CAPE ANN CLASSIC CARS Show

free · Benefits Gloucester Meetinghouse Foundation

Please join us for a day of family fun with beautiful vintage cars displayed on the green in front of the Meetinghouse.

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