Entertainment events in Gloucester

Check out happening entertainment events all around Gloucester, MA

Gloucester Waterfront Festival

 Sat, 15 Aug at 09:00 am Stage Fort Park

Fast Times

 Sat, 04 Apr at 08:00 pm The Cut Live

Ryan Montbleau Band with Wood & Bone

 Sat, 11 Apr 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

Pride Blast Off

 Sat, 30 May at 08:00 pm The Cut Live

Spring Fundraiser Social for Cape Ann Pride

 Wed, 25 Mar at 06:00 pm Minglewood Harborside

Dead to the Core March Show

 Fri, 27 Mar at 08:00 pm The Cut Live

The Cold Stares

 Thu, 26 Mar at 08:00 pm The Cut Live

Music at the Beach Fundraiser at The Cut

 Thu, 30 Apr at 07:00 pm The Cut Live

A Night of Comedy with Steve Sweeney and Carolyn Plummer & Dan Crohn

 Sat, 02 May at 07:30 pm The Cut Live

"Out By the Ocean" Kick-Off Party for Cape Ann Pride 2026

 Thu, 28 May at 05:00 pm DRIFT Gloucester

4EverFab at Gloucester Summer Concert Series

 Sun, 26 Jul at 06:30 pm Stage Fort Park

The Samples

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

A Vivaldi & Mozart Candlelight Experience In Gloucester, MA🕯️Saturday 28th March

 Sat, 28 Mar at 10:00 pm Gloucester Unitarian Universalist Church

Didgeridoo Sound/ Color Vibrational Attunement, Meditation & Sound Bath Experience

 Sun, 29 Mar at 06:00 pm Floating Lotus Gloucester

A Farewell to Kings - Rush Tribute

 Thu, 14 May at 07:30 pm The Cut Live

The Clements Brothers

 Thu, 23 Apr at 07:30 pm The Cut Live

GUS Rocks The Cut

 Sat, 28 Mar at 06:00 pm The Cut Live

The Hot Tub Piranhas will be ROCKIN' Minglewood Harborside!

 Fri, 10 Apr at 09:00 pm Minglewood Harborside

SWING DANCE

 Sun, 12 Apr at 06:00 pm Capt. Lester S. Wass American Legion Post 3

Piano Bar with Jack Favazza - A Fundraiser for Veterans' Easter Meals

 Fri, 27 Mar at 07:30 pm Capt. Lester S. Wass American Legion Post 3

Chosen one album release party

 Sat, 04 Apr at 09:00 pm Minglewood Harborside

LIVE FROM THE LOUNGE - Dogtown Duo

 Sat, 04 Apr at 08:00 pm Capt. Lester S. Wass American Legion Post 3

SWING DANCE

 Sun, 10 May at 06:00 pm Capt. Lester S. Wass American Legion Post 3

Wine Glass Paint Party!

Thu, 09 Apr at 06:00 pm 27 Lexington Ave, Gloucester, Ma

OCW: Eye Of The Storm

 Sat, 25 Apr at 06:00 pm Magma USD 23

A Film-in-Process Screening & Q&A for THE GATE

 Wed, 17 Jun at 06:00 pm The Historic Ben Butler Homestead Free