Upcoming Gloucester Events

Check out what's happening 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

Cape Ann Big Band New Year’s Concert

 Fri, 02 Jan at 07:30 pm 10 Church St, Gloucester, MA, United States, Massachusetts 01930

Holiday Drag Bingo

 Fri, 19 Dec at 06:30 pm 1 Lexington Ave, Gloucester, MA, United States, Massachusetts 01930

Elemental Balancing Experience in the Salt Cave

 Sat, 27 Dec at 06:30 pm 232 Main Street, Gloucester, MA, United States, Massachusetts 01930

An Enchanted Evening of Winter Solstice Ritual & Mediumship

 Sat, 20 Dec at 06:30 pm 232 Main St USD 55

A Special Film Screening: TOWNIE, Starring Steve Sweeney

 Fri, 16 Jan at 07:30 pm The Cut Live

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

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

Santa Retruns to the Castle

Sun, 14 Dec at 04:00 pm 80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930

F-BOMB PRE-XMAS PARTY

 Sat, 13 Dec at 09:00 pm Minglewood Harborside

Dead to the Core - January Show

 Fri, 23 Jan at 08:00 pm The Cut Live

An Enchanting Evening of Winter Solstice Ritual & Mediumship

 Fri, 19 Dec at 06:30 pm 232 Main St USD 55

Deck the Halls by Candlelight at Hammond Castle Museum

 Thu, 18 Dec at 05:30 pm 80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930

Masshole Walking Group

 Thu, 18 Dec at 06:00 pm 137 Main St, Gloucester, MA, United States, Massachusetts 01930

Livin' On Luck at Salted Cod

 Fri, 13 Feb at 07:00 pm Salted Cod Arthouse & Wine Bar Free

Acoustic View Bill Dwyer &Friends

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

Plunge for Pete

 Sat, 27 Dec at 10:30 am Bass Rocks, Gloucester, MA

Deck the Halls at Hammond Castle Museum

 Sun, 14 Dec at 09:00 am 80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930

Last Minute Holiday Market at The Cut!

 Sun, 21 Dec at 12:00 pm 177 E Main St, Gloucester, MA 01930-3801, United States

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

LIVE FROM THE LOUNGE - ToniAnn Enes

 Sat, 31 Jan at 07:00 pm 8 Washington St, Gloucester, MA 01930-5734, United States

Sound Healing Bath in the Salt Cave

 Fri, 16 Jan at 06:00 pm 232 Main St USD 61

Annie Brobst with Whiskey-6 & Ross Livermore

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

December Vacation Classes at Art Haven: Grades K-5th

 Fri, 26 Dec at 09:00 am 20 Maplewood Ave, Unit 3, Gloucester, MA, United States, Massachusetts 01930

`14th Annual Spruce Road Extravaganza

 Sat, 20 Dec at 06:00 pm Blue Collar Lobster Company USD 100

Wintersong: A Celtic Advent Meditation

 Tue, 16 Dec at 07:00 pm 1123 Washington St, Gloucester, MA, United States, Massachusetts 01930

Music Video Bingo in our Pub

Tue, 16 Dec at 07:30 pm 53 Gloucester Ave, Gloucester, MA, United States, Massachusetts 01930

Super Bowl Party

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

Deck the Halls of Hammond Castle Museum: Self-Guided Exploration from Boston

 Sun, 14 Dec at 10:30 am Hammond Castle

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

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

The Nectar Exchange

 Mon, 05 Jan at 06:30 pm 6 Lexington Ave., Magnolia, MA, United States, Massachusetts 01930

Meet Santa!

 Sun, 14 Dec at 11:00 am Harbor 9 Golf

Elemental Balancing Experience in the Salt Cave

Sat, 27 Dec at 06:30 pm Gloucester Massahusetts

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

Left Right Center Tournament

 Sat, 17 Jan at 07:00 pm The Elks at Bass Rocks

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

Holiday Sip & Shop Open House

Sat, 20 Dec at 12:00 pm Lighthouse Marina

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

Peter Pan

 Sun, 21 Dec at 03:30 pm 10 Church St, Gloucester, MA, United States, Massachusetts 01930

New Year's Day: Rhythm in Flow

 Thu, 01 Jan at 11:00 am 3A Pond Road, Gloucester, MA, United States, Massachusetts 01930

Muddy Ruckus at The Rhumb Line

 Fri, 26 Dec at 08:30 pm The Rhumb Line

Marshalls farmstand holiday fair

 Sun, 14 Dec at 10:00 am Marshall's Farm Stand & Greenhouses

5th Annual Gloucester’s So Salty

 Sat, 24 Jan at 10:00 am 27 Pleasant St, Gloucester, MA, United States, Massachusetts 01930

The Spynz - Third Thursday (music) Therapy FREE Show

 Thu, 18 Dec at 07:00 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

Shared Breath, Shared Song

 Sun, 14 Dec at 04:00 pm Gloucester Unitarian Universalist Church

CAM Talk: 100 years in 20 Minutes—The Story of Granite Quarrying on Cape Ann, by Monica Lawton

 Sat, 10 Jan at 03:00 pm Cape Ann Museum Green, 13 Poplar Street, Gloucester, MA

December 22nd: Jingle Bar at Beauport Hotel

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

Bowl the Man Down 2

 Sun, 14 Dec at 01:00 pm Cape Ann Lanes

SAFETY - THE NYE EXTRAVAGANZA - Late Show

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

Gloucester Gratis Days During Deck the Halls at Hammond Castle Museum

 Tue, 16 Dec at 09:00 am 80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930

CHRISTMAS KIDS PARTY @ AMERICAN LEGION POST 3!!!

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

Children & Family Workshop (Free) with Loren Doucette

 Sat, 10 Jan at 01:00 pm 1 Lexington Ave, Gloucester, MA, United States, Massachusetts 01930

Breakfast with Santa

 Sun, 14 Dec at 09:00 am Castle Manor Inn

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

The Gloucesterman Adventure: Jonathan Bayliss and Schooner Adventure at 100

 Thu, 29 Jan at 05:30 pm Sawyer Free Library Free

Minglewood Winter Market

 Sun, 21 Dec at 02:00 pm Minglewood Harborside

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

Traditional & Contemporary St. Lucia hymns & procession

 Sun, 14 Dec at 10:00 am St. Paul Lutheran Church, 1123 Washington St, Gloucester, MA, United States, Massachusetts 01930

Bob Marley night

 Fri, 20 Feb at 09:00 pm Minglewood Harborside

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

Holidays With The Bordellos!!

 Sun, 21 Dec at 05:30 pm The Rhumb Line

Christmas at the Magee's

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

Jeff Fraser solo at the Beauport

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

Light in the Darkness. An Evening of Hope and Joy at Open Art Studio

Sun, 14 Dec at 05:00 pm UCC Magnolia 3 Norman Ave, Magnolia, MA

Shop Until 9 PM

 Thu, 18 Dec at 10:00 am Main Street, Gloucester, MA, United States, Massachusetts 01930

Yin Yoga & Yin Magic

 Thu, 01 Jan at 05:30 pm 6 Lexington Ave., Magnolia, MA, United States, Massachusetts 01930
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