Entertainment events in Gloucester

Check out happening entertainment events all around Gloucester, MA

Booty Vortex - Boston's Finest Funk and Disco Band at The Cut

 Sat, 11 Oct at 08:30 pm The Cut Live

Rock & Roll Circus Starring James Montgomery, Jon Butcher, and Danny Klein

 Fri, 07 Nov at 08:00 pm The Cut Live

Convergence: Trio Gaia in Recital

 Fri, 10 Oct at 07:30 pm 10 Church St, Gloucester, MA, United States, Massachusetts 01930

LIVE FROM THE LOUNGE - Jake Pardee

 Sat, 11 Oct at 08:00 pm 8 Washington St, Gloucester, MA 01930-5734, United States

The Warped Tour Band

 Fri, 10 Oct at 08:00 pm The Cut Live

Dead to the Core - Fall Tour

 Sat, 18 Oct at 08:00 pm The Cut Live

Moss Henry Live at Lobsta Land

Fri, 03 Oct at 05:00 pm Lobsta Land Restaurant

Live music with Bill Toomey

 Sat, 04 Oct at 05:00 pm 75 Essex Ave (Rt. 133), Gloucester, MA, United States, Massachusetts 01930

Comedy & Conversations; Navigating Menopause

 Thu, 16 Oct at 07:00 pm 232 Main Street, Gloucester, MA, United States, Massachusetts 01930

Muddy Ruckus - Halloween at The Rhumb Line!

 Fri, 31 Oct at 09:30 pm The Rhumb Line

SAFETY - The Neverending Safety Show - 80s Fantasy & Magic

 Fri, 24 Oct at 08:30 pm 177 Main Street, Gloucester, MA, United States, Massachusetts 01930

Fast Times - 80’s Music

 Sat, 08 Nov at 08:00 pm The Cut Live

Soul Rebel Project - The Halloween Show

 Fri, 31 Oct at 09:00 pm 177 Main Street, Gloucester, MA, United States, Massachusetts 01930

SKUNK HALLOWEEN AT THE CUT, with Liquid light Bros, and four special musical guests

Sat, 25 Oct at 08:00 pm The Cut Live

The NONNAS Dinner

 Sun, 19 Oct at 02:00 pm 2 Main St., Gloucester, MA, United States, Massachusetts 01930

Cape Ann Makers Market at Magtoberfest 2025

 Sun, 12 Oct at 11:00 am Magnolia Library and Community Center

Moss Henry Live at Lobsta Land

 Sat, 04 Oct at 05:00 pm Lobsta Land Restaurant

Rhythm of The Saints Tribute to Paul Simon with Special Guest Gary Backstrom Band

 Fri, 28 Nov at 08:00 pm The Cut Live

Lez Zeppelin Earl's Court '75: The Greatest Led Zeppelin Show Performed in its Entirety

 Fri, 03 Oct at 08:30 pm 177 Main Street, Gloucester, MA, United States, Massachusetts 01930

The Influence Event 2025

 Wed, 22 Oct at 05:30 pm The Cut - Stage • Studio • Restaurant • Bar USD 80

5th Annual Magtoberfest

 Sun, 12 Oct at 11:00 am 1 Lexington Ave, Gloucester, MA, United States, Massachusetts 01930

FJ - A Tribute To Foreigner & Journey

 Fri, 21 Nov at 08:00 pm The Cut Live

Live Band Karaoke Showcase with Groove Therapy - hosted by DJ Lou

 Fri, 17 Oct at 07:00 pm The Cut Live

Live Music with John Jerome

 Fri, 03 Oct at 05:00 pm 75 Essex Ave (Rt. 133), Gloucester, MA, United States, Massachusetts 01930

Phantom of the Opera with Live Accompaniment by Peter Krasinski

 Sun, 26 Oct at 06:30 pm 80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930

Live Music with local talent Steve Dennis

 Sat, 11 Oct at 05:30 pm 75 Essex Ave (Rt. 133), Gloucester, MA, United States, Massachusetts 01930

Live Music with Dan King

 Fri, 10 Oct at 05:30 pm 75 Essex Ave (Rt. 133), Gloucester, MA, United States, Massachusetts 01930

O'Brien's OBoru @ Blue Collar Lobster

 Sun, 16 Nov at 03:30 pm Blue Collar Lobster Co.

Beck-Ola

 Sat, 06 Dec at 07:00 pm The Cut Live

The Body Remembers, The Body Rewrites: A Community Workshop

 Sat, 25 Oct at 01:00 pm Movement Arts Gloucester MA USD 0 to 23

Live Music with Matt Rich on the Sun Deck or Bridge Deck

 Sun, 12 Oct at 05:00 pm 75 Essex Ave (Rt. 133), Gloucester, MA, United States, Massachusetts 01930

GLOUCESTER MEETINGHOUSE 2025-26 SERIES OPENS OCT. 10WITH NEW ENGLAND CONSERVATORY’S ‘TRIO GAIA’

 Fri, 10 Oct at 07:30 pm Gloucester Unitarian Universalist Church

Danielia Cotton with Megan Wolffe

 Thu, 13 Nov at 07:30 pm The Cut Live

Metropolis with Live Accompaniment by Peter Krasinski

 Mon, 27 Oct at 06:30 pm 80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930

O'Brien's OBoru @ Blue Collar Lobster

 Sun, 26 Oct at 03:30 pm Blue Collar Lobster Co.

Private event- DJ holiday party

 Fri, 12 Dec at 06:00 pm Beauport Hotel Gloucester

CAST's Production of Two Gentlemen of Verona

 Fri, 14 Nov at 07:00 pm Capt. Lester S. Wass American Legion Post 3