Gloucester Arts Events

Back to Black LIVE: An Amy Winehouse Tribute Starring Megan Wolffe

The Cut Live 7 Feb 2026

Little Lies - A Tribute to Fleetwood Mac

The Cut Live 6 Feb 2026

Bridgerton Ball

80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930 28 Feb 2026

Beauport Hospitality Group Wedding Showcase 2026

Cruiseport Gloucester 1 Feb 2026

JWC Focaccia Garden Art

37 Main Street, Gloucester, MA, United States, Massachusetts 01930 1 Feb 2026

Terrafunk & The Rupert Selection

The Cut Live 5 Feb 2026

Mardi Gras with the Jambalaya Horns

177 Main Street, Gloucester, MA, United States, Massachusetts 01930 13 Feb 2026

Scotty Austin - The Northeast Invasion Tour

The Cut Live 29 Jan 2026

Kids' Free Week During School Vacation Week

80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930 16 Feb 2026

The Super 70s Rock Show

177 Main Street, Gloucester, MA, United States, Massachusetts 01930 30 Jan 2026

Dead to the Core - January Show

The Cut Live 23 Jan 2026

Fish Tales: CAPE ANN ADVENTURES

126 E Main St, Gloucester, MA, United States, Massachusetts 01930 29 Jan 2026

Bridgerton Afternoon Tea at the Castle

80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930 28 Feb 2026

2nd Annual Driving for Dollars Virtual Golf Charity Event

Harbor 9 Golf 5 Feb 2026

Cabot Potions & Philters II w/ Priest Kevin Inman & Rev. Jacq Civitarese

5 Short Street , Gloucester, MA, United States, Massachusetts 01930 28 Feb 2026

Annual Annsiquam Village Players' Winter Cabaret

Annisquam Village Hall 7 Feb 2026

Coffee & Conversations: Quarry Inspirations—Art & Architecture

CAM Green, 13 Poplar St, Gloucester, MA 22 Jan 2026

Burns Night Ceilidh

11 Pleasant St., Suite 64, Gloucester, MA, United States, Massachusetts 01930 25 Jan 2026