Upcoming Gloucester Events

Check out what's happening all around Gloucester, MA

Gloucester Waterfront Festival

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

Lily Jean Benefit Concert

 Sun, 17 May at 12:00 pm The Cut Live

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

Neon 90's at Minglewood

 Sat, 02 May at 09:00 pm Minglewood Harborside

Pride Blast Off

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

Easter by the Sea Buffet

Sun, 05 Apr at 10:00 am 55 Commercial St, Gloucester, MA, United States, Massachusetts 01930

Spring Fundraiser Social for Cape Ann Pride

 Wed, 25 Mar at 06:00 pm Minglewood Harborside

Beauport Cruiselines Easter at Sea

 Sun, 05 Apr at 12:00 pm 6 Rowe Sq, Gloucester, MA

Dead to the Core March Show

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

April Wine Dinner

 Thu, 30 Apr at 06:00 pm Central Gloucester

The Cold Stares

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

Businesswomen's Committe Luncheon: Wave Makers ~ Tide Changers: Women of Innovation & Impact

 Thu, 30 Apr at 11:00 am Beauport Hotel Gloucester

Music at the Beach Fundraiser at The Cut

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

St. Peter's Fiesta 5K Road Race

 Thu, 25 Jun at 06:30 pm Stage Fort Park

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

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

Twin Lights Half Marathon

 Sun, 03 May at 08:00 am Good Harbor Beach

"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

Twin Lobster Half Marathon

 Sun, 07 Jun at 08:00 am Gloucester High School

The Samples

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

Cape Ann Artisans Open Studios - Spring Event

 Sat, 06 Jun at 10:00 am Gloucester and Rockport MA Free

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

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

A Spring Night Out - With Senator Bruce Tarr

 Fri, 27 Mar at 07:00 pm The Gloucester House

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

Richard III

 Thu, 09 Apr at 07:30 pm Gloucester Stage

AD/HD @ Minglewood Harborside!

 Sat, 18 Jul at 08:00 pm Minglewood Harborside

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

CAM Talk: Artist Conversations Across Time: From Cape Ann to Rembrandt in Rothko’s “Thru the Window"

 Wed, 03 Jun at 02:00 pm Cape Ann Museum Green, 13 Poplar St, Gloucester, MA, 01930

K-Pop Demon Hunters Dance Party & Sing-A-Long

 Sun, 19 Apr at 01:00 pm 177 Main St, Gloucester, MA 01930-5703, United States

SWING DANCE

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

Less Than Zero @ DRIFT Gloucester

 Fri, 27 Mar at 09:00 pm DRIFT Gloucester

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

Allegra and the Daydreamers at Drift

Fri, 03 Apr at 09:00 pm DRIFT Gloucester

CAM Talk: To Live like an Artist, Cape Ann of the 1920s, by Martha Oaks

 Wed, 22 Apr at 02:00 pm Cape Ann Museum Green, 13 Poplar St, Gloucester, MA

POKER RUN

 Sat, 16 May at 11:00 am Capt. Lester S. Wass American Legion Post 3

2026 Education & Workforce Development Conference

 Thu, 16 Apr at 08:30 am Cruiseport Gloucester USD 0 to 100

LIVE FROM THE LOUNGE - Dogtown Duo

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

Livin' On Luck at Salted Cod, Gloucester

 Fri, 27 Mar at 07:00 pm Salted Cod Arthouse Free

Market At Minglewood

Sat, 04 Apr at 11:00 am Main Street, Gloucester, MA

April Vacation at Art Haven: Grades K-5th

 Mon, 20 Apr at 09:00 am 20 Maplewood Ave, Unit 3, Gloucester, MA, United States, Massachusetts 01930

Preseason Bowling Night - 2026

 Sun, 29 Mar at 04:00 pm Cape Ann Lanes/ Laneside Pub & Brewery USD 23

Mile Marker Cape Ann Marina

 Sat, 29 Aug at 06:00 pm Mile Marker One

Square-Foot Gardening Workshop

 Sat, 02 May at 09:30 am 103 R Maplewood Ave, Gloucester, MA, United States, Massachusetts 01930

Dock & Dine at Mile Marker One

 Thu, 21 May at 05:00 pm Mile Marker One Restaurant & Igloo DIning Free

Spike the Punch at Minglewood

 Fri, 10 Jul at 09:00 pm The Minglewod Gloucester MA

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

Livin' On Luck at The Salted Cod, Gloucester

 Fri, 24 Apr at 07:00 pm Salted Cod Arthouse Free

Livin' On Luck at The Salted Cod, Gloucester

 Fri, 15 May at 07:00 pm 53 Rocky Neck Ave Free

Gloucester LOVE Scavenger Hunt for Couples Date Night!!

 Thu, 26 Mar Recommended scavenger starting point or other city spot of your choice! (YOU MUST USE PDF TICKETS EMAILED FOR EVENT- NO MOBILE APP OR QR CODES ACCEPTED) USD 10

Paula Borsetti Art Demonstration

 Sat, 11 Apr at 04:00 pm Central Gloucester

Annual Freighttrain BBQ!!!!

Sat, 08 Aug at 02:00 pm 5 Forest St. Gloucester ma
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