Upcoming Gloucester Events

Check out what's happening all around Gloucester, MA

Bridgerton Afternoon Tea at the Castle

 Sat, 28 Feb at 01:00 pm 80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930

Bridgerton Ball

 Sat, 28 Feb at 06:00 pm 80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930

Fast Times

 Sat, 04 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

Nirvani - A Nirvana Tribute Experience with Foo!

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

Piano Bar with Jack at Saluti Wine Bar

 Fri, 20 Feb at 07:00 pm Saluti

Pride Blast Off

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

Altan

 Fri, 20 Mar at 08:00 pm The Cut Live

GHS Fundraiser for class of 2027 with KICKED OFF THE BUS AND OLD HICKORY BOULEVARD

Sun, 08 Mar at 06:30 pm The Cut Live

Mad Science at the Castle

Sat, 07 Mar at 11:00 am 80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930

LCR Tournament To Benefit The Families of The F/V Lily Jean

Sat, 28 Feb at 06:00 pm St Peters Club

A Princess Experience

 Sat, 14 Mar at 10:30 am 80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930

Spring Fundraiser for Cape Ann Pride

 Wed, 25 Mar at 06:00 pm Minglewood Harborside

Left Right Center Tournament

 Sat, 28 Feb at 07:00 pm The Elks at Bass Rocks

Neon 90's at Minglewood

 Sat, 02 May at 08:00 pm Minglewood Harborside

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

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

Big Ol' Dirty Bucket - Third Thursday (music) Therapy FREE Show

 Thu, 19 Feb at 07:00 pm The Cut Live

Twin Lights Half Marathon

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

Dueling Pianos

 Fri, 06 Mar at 08:00 pm 177 Main Street, Gloucester, MA, United States, Massachusetts 01930

A Taste of Two Valleys Wine Dinner

 Thu, 26 Feb at 06:00 pm Central Gloucester

February Song Swap with Brian King, Susan Cattaneo, & Miranda Aisling

 Sun, 22 Feb at 07:00 pm 11 Pleasant St., Suite 64, Gloucester, MA, United States, Massachusetts 01930

Bob Marley night

 Fri, 20 Feb at 09:00 pm Minglewood Harborside

Veuve "Clicquot in the Snow" 2026

 Sat, 21 Feb at 07:00 pm Beauport Hotel Gloucester USD 13

Magic Show with Robert Clarke

 Sun, 15 Mar at 01:00 pm The Cut Live

Cape Ann Artisans Open Studios - Spring Event

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

Business After Hours at Saluti Wine Bar

 Wed, 18 Feb at 05:00 pm Saluti

Gloucester LOVE Scavenger Hunt for Couples Date Night!!

 Thu, 19 Feb 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

Morning Momentum: Conversations that "Break the Ice"

 Thu, 05 Mar at 08:30 am Mile Marker One

Story Songs: Cat Stevens, Gordon Lightfoot, and Harry Chapin- Winter Edition!

 Sat, 21 Mar at 07:30 pm The Cut Live

Chosen one album release party

 Sat, 04 Apr at 09:00 pm Minglewood Harborside

AD/HD @ Minglewood Harborside!

 Sat, 18 Jul at 08:00 pm Minglewood Harborside

Left Right Center Tournament

 Sat, 21 Mar at 07:00 pm The Elks at Bass Rocks

The Cold Stares

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

Yin Yoga & Yin Magic

 Thu, 26 Feb at 05:30 pm 6 Lexington Ave., Magnolia, MA, United States, Massachusetts 01930

Bowl to Build School Gardens

 Sun, 15 Mar at 04:00 pm Cape Ann Lanes/ Laneside Pub & Brewery USD 29

Birding Cape Ann, MA

 Sat, 21 Feb at 09:00 am Jodrey State Fish Pier Free

GUS Rocks The Cut

 Sat, 28 Mar at 06:00 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

Space Moose at The Rhumb Line Gloucester, MA Sat March 14th 8:30pm start time!!

Sat, 14 Mar at 08:30 pm The Rhumb Line

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

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

Your Inner Boss Leadership Retreat: Reset, Rebuild & Rise Into 2026

 Fri, 06 Mar at 04:00 pm Beauport Hotel Gloucester USD 375 to 1,650

Purim Celebration & Grand Hamantash Bake

 Tue, 03 Mar at 05:00 pm 37 Main Street, Gloucester, MA, United States, Massachusetts 01930

SWING DANCE

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

Community Contra Dance at MAGMA Gloucester

 Sat, 07 Mar at 07:00 pm MAGMA Gloucester

KIDS EVENT! - Meet Elsa from Frozen!

 Sun, 22 Feb at 10:00 am Capt. Lester S. Wass American Legion Post 3

14th Annual Charles Olson Lecture

 Sat, 07 Mar at 02:00 pm CAM Green, 13 Poplar St, Gloucester, MA

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

 Sat, 28 Feb at 07:00 pm 5 Short Street , Gloucester, MA, United States, Massachusetts 01930

Neon 90’s at The Cut

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

K-Pop Demon Hunters Dance Party and Sing-A-Long - 12:00 PM

 Sun, 01 Mar at 12:00 pm The Cut Live

Veuve Clicquot Brunch by the Sea

 Sun, 22 Feb at 11:30 am 55 Commercial St, Gloucester, MA, United States, Massachusetts 01930

Jeff Fraser at The Cut in Gloucester

 Fri, 13 Mar at 07:00 pm The Cut Live

Live Music Tuesdays

Tue, 17 Feb at 06:00 pm 55 Commercial St, Gloucester, MA, United States, Massachusetts 01930

Spring Seed Giveaway

 Sat, 07 Mar at 09:30 am 103 R Maplewood Ave, Gloucester, MA, United States, Massachusetts 01930

SWING DANCE

 Sun, 08 Mar at 06:00 pm Capt. Lester S. Wass American Legion Post 3

Square-Foot Gardening Workshop

 Sat, 14 Mar at 09:30 am 103 R Maplewood Ave, Gloucester, MA, United States, Massachusetts 01930

Bordellos at The Rhumb Line!!

 Sun, 22 Feb at 05:30 pm The Rhumb Line

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

Chip Rockers & Dog Town - Third Thursday (music) Therapy FREE Show

 Thu, 19 Mar at 08:30 pm The Cut Live

Marketing 101: How to Get Results on Any Budget

 Thu, 26 Feb at 05:30 pm 24 Harbor Loop, Gloucester, MA, United States, Massachusetts 01930

Allegra and the Daydreamers at Drift

Fri, 03 Apr at 09:00 pm DRIFT Gloucester

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

OCW: Incarcerated

 Sat, 28 Feb at 05:30 pm Magma USD 23

2026 Education & Workforce Development Conference

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

Piano Bar at Beauport Hotel

 Thu, 19 Feb at 06:00 pm 55 Commercial St, Gloucester, MA, United States, Massachusetts 01930

Spike the Punch at Minglewood

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

The History of Medieval Arms & Armor and Self-Guided Tours

 Fri, 20 Feb at 10:30 am 80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930

Square-Foot Gardening Workshop

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

Gentle Yoga with Melanie at Revive Wellness

 Wed, 18 Feb at 09:00 am 232 Main Street, Gloucester, MA, United States, Massachusetts 01930

Spring Seed Giveaway Drop-in Hours

 Mon, 09 Mar at 10:00 am 103 R Maplewood Ave, Gloucester, MA, United States, Massachusetts 01930

4EverFab at Gloucester Summer Concert Series

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

Wine Glass Paint Party!

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

Somatic Reset Workshop: From Winter Bracing to Spring Flow

 Sat, 28 Feb at 03:00 pm 3A Pond Road, Gloucester, MA, United States, Massachusetts 01930

SWING DANCE

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

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

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

Restorative Flow Yoga with Chelsea at Revive Wellness

 Tue, 17 Feb at 07:00 pm 232 Main Street, Gloucester, MA, United States, Massachusetts 01930

Music Video Bingo in our Pub

Tue, 17 Feb at 07:30 pm 53 Gloucester Ave, Gloucester, MA, United States, Massachusetts 01930

Intimate First-Time Homebuyer Seminar

 Mon, 02 Mar at 05:30 pm The Amanda Armstrong Group Office Free

The Nectar Exchange

 Mon, 09 Mar at 06:30 pm 6 Lexington Ave., Magnolia, MA, United States, Massachusetts 01930

Jeff Fraser solo at the Beauport

Tue, 17 Feb at 06:00 pm Beauport Hotel Gloucester

AI For Small Business

 Wed, 11 Mar at 08:30 am 24 Harbor Loop, Gloucester, MA, United States, Massachusetts 01930

Info Session: How to Volunteer in Your Community with Backyard Growers

 Thu, 05 Mar at 05:00 pm Sawyer Free Library

Author Reading: The Idea of Light

 Sat, 07 Mar at 03:00 pm Magnolia Library and Community Center

KPop Huntrix Concert Experience and Meet & Greet

 Wed, 18 Feb at 06:00 pm 80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930

The Nectar Exchange

 Mon, 02 Mar at 06:30 pm 6 Lexington Ave., Magnolia, MA, United States, Massachusetts 01930

Paula Borsetti Art Demonstration

 Sat, 11 Apr at 04:00 pm Central Gloucester

Five-Three or Two Day BareBones Woodcarving Workshop

 Mon, 16 Feb at 09:00 am 235 E Main St, Gloucester, MA, United States, Massachusetts 01930

Bloody Mary Sunday with Jack Favazza

 Sun, 22 Mar at 11:00 am Gloucester MA Elks Lodge #892