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 John Baboian Guitar Ensemble
Fri · July 10, 2026 · 6:00pm

The John Baboian Guitar Ensemble

Benefits TownGreen · Food by Meat & Sweet

The John Baboian Ensemble with vocalist Sandi Bedrosian. Well known as an accomplished guitarist and composer in jazz and swing circles, John Baboian is…

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Headlands
Fri · July 24, 2026 · 6:00pm

Headlands

Free, Donations Encouraged. · Benefits Backyard Growers · Food by The Lobster Roller

They’re Back! With their exciting three-part vocals that put their stamp on whichever musical genre they choose, HEADLANDS has been playing at clubs,…

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Rhiannon Hurst & Friends
Fri · July 31, 2026 · 6:00pm

Rhiannon Hurst & Friends

Free, Donations Encouraged. · Benefits Pathways for Children · Food by Crepes du jour

Rhiannon Hurst earned some serious respect in the jazz world even before she graduated high school. She won 2nd place in the Berklee International High School…

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HYE Fusion, Middle Eastern Band
Fri · August 7, 2026 · 6:00pm

HYE Fusion, Middle Eastern Band

Free, Donations Encouraged. · Benefits Gloucester Education Fund · Food by Meat & Sweet

This trio of classically trained musicians blends Western jazz favorites with the irresistible rhythms and melodies of their Middle Eastern backgrounds for a…

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What Time Is It, Mr. Fox?
Fri · August 21, 2026 · 6:00pm

What Time Is It, Mr. Fox?

Free, Donations Encouraged. · Benefits The Grace Center · Food by Markouk Bread

Singer/songwriter 3rian King and the musicians of What Time Is It Mr. Fox? deliver an electrifying performance with an evening of smoky cabaret, neo-soul, and…

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Jim ‘n’ Tonic
Sat · August 29, 2026 · 6:00pm

Jim ‘n’ Tonic

Benefits Action, Inc. · Food by Crepes du jour

Please join us on Friday, August 29th in front of the Gloucester Unitarian Universalist Church, corner of Middle and Church Streets, Gloucester, for Jim…

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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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