Entertainment events in Gloucester

Check out happening entertainment events all around Gloucester, MA

Firebird Pops Orchestra Presents Christmas at the Castle

 Fri, 19 Dec at 05:30 pm 80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930

BrassFed Nation's Holiday Bash

 Fri, 19 Dec at 07:30 pm 177 Main Street, Gloucester, MA, United States, Massachusetts 01930

Battle of the Bands Alumni - Fundraiser for the Gloucester Public Schools Band Programs

 Sat, 27 Dec at 05:30 pm The Cut Live

F-BOMB PRE-XMAS PARTY

 Sat, 13 Dec at 09:00 pm Minglewood Harborside

Acoustic View Bill Dwyer &Friends

 Sat, 20 Dec at 08:00 pm Snug Harbor Studio 39 Ye Olde County Rd Gloucester

Glitz & Glam NYE 2026 Party at Harbor 9

 Wed, 31 Dec at 07:30 pm Harbor 9 Golf & Sports Bar USD 29 to 322

Nirvani - A Nirvana Tribute Experience with Foo!

 Sat, 07 Mar at 08:00 pm 177 Main Street, Gloucester, MA, United States, Massachusetts 01930

Annie Brobst with Whiskey-6 & Ross Livermore

 Sat, 17 Jan at 08:00 pm The Cut Live

Super Bowl Party

 Sun, 08 Feb at 07:00 pm The Cut Live

It's The 3rd Annual Very Mixtape Christmas @ The Rhumb Line!

 Sat, 20 Dec at 08:30 pm The Rhumb Line

Live Music with Peter Tentido

 Thu, 18 Dec at 05:00 pm 75 Essex Ave (Rt. 133), Gloucester, MA, United States, Massachusetts 01930

LIVE from the LOUNGE - INGE BERGE

 Sat, 17 Jan at 08:00 pm Capt. Lester S. Wass American Legion Post 3

A Very Jack Favazza Christmas - Fundraiser for Veterans' Holiday Meals

 Sat, 20 Dec at 01:00 pm Capt. Lester S. Wass American Legion Post 3

Eagle in the Attic at Minglewood 12/26

 Fri, 26 Dec at 09:00 pm Minglewood Harborside

The Super 70s Rock Show

 Fri, 30 Jan at 08:00 pm 177 Main Street, Gloucester, MA, United States, Massachusetts 01930

Little Lies - A Tribute to Fleetwood Mac

 Fri, 06 Feb at 08:00 pm The Cut Live

December 17th: Jingle Bar at Beauport Hotel

 Wed, 17 Dec at 06:00 pm Beauport Hotel Gloucester

The Beautiful Losers - A Tribute to Bob Seger & The Silver Bullet Band

 Sat, 24 Jan at 08:00 pm The Cut Live

Mardi Gras with the Jambalaya Horns

 Fri, 13 Feb at 07:30 pm 177 Main Street, Gloucester, MA, United States, Massachusetts 01930

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

 Sat, 07 Feb at 08:00 pm The Cut Live

SAFETY - THE NYE EXTRAVAGANZA - Late Show

 Wed, 31 Dec at 07:30 pm The Cut Live

December 22nd: Jingle Bar at Beauport Hotel

 Mon, 22 Dec at 06:00 pm Beauport Hotel Gloucester USD 18 to 162

CHRISTMAS KIDS PARTY @ AMERICAN LEGION POST 3!!!

 Sun, 21 Dec at 01:00 pm Capt. Lester S. Wass American Legion Post 3

Don't Stop Believin, Live Band Karaoke Showcase with Groove Therapy - hosted by DJ Lou

 Sat, 14 Feb at 08:00 pm The Cut Live

2026 Endless Night Vampire Salon: HAMMOND CASTLE

 Fri, 22 May at 07:00 pm Hammond Castle Museum USD 49 to 186

Scotty Austin - The Northeast Invasion Tour

 Thu, 29 Jan at 06:45 pm The Cut Live

Mixtape Misfits: 90's & 2000's Rock Tribute LIVE @ The Rhumb Line

 Fri, 20 Feb at 08:30 pm The Rhumb Line

Lobster Trap Menorah Lighting

 Tue, 16 Dec at 06:00 am Temple Ahavat Achim

Christmas at the Magee's

Wed, 24 Dec at 03:00 pm 5 forest street Gloucester ma