All Upcoming events

• Sat, 29 Nov, 2025 - 06:30 PM

  Kevin Coan - World Renowned Spirit Medium

  Capt. Lester S. Wass American Legion Post 3

  83+ Interested
• Sat, 13 Dec, 2025 - 08:00 PM

  HOLIDAYS & WINTERTIDE A night of Christmas and Winter Music

  The Cut Live

  24+ Interested
• Sat, 15 Nov, 2025 - 07:30 PM

  ‘Cold Chocolate’ debuts on Cape Ann, Saturday, Nov. 15th

  Gloucester Unitarian Universalist Church
• Fri, 19 Dec, 2025 - 05:30 PM

  Firebird Pops Orchestra Presents Christmas at the Castle

  80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930

  43+ Interested
• Sat, 15 Nov, 2025 - 07:30 PM

  An Evening with Cold Chocolate

  10 Church St, Gloucester, MA, United States, Massachusetts 01930

  9+ Interested
• Fri, 14 Nov, 2025 - 08:00 PM

  DMTB - A Celebration of Dave Matthews Band

  The Cut Live

  34+ Interested
• Fri, 21 Nov, 2025 - 09:00 AM

  Deck the Halls at Hammond Castle Museum

  80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930

  52+ Interested
• Sat, 06 Dec, 2025 - 07:00 PM

  Ladies Pre-Chanukah Resin Menorah

  37 Main Street, Gloucester, MA, United States, Massachusetts 01930
• Sat, 06 Dec, 2025 - 06:00 PM

  Miranda Aisling Concert at Rocky Neck Cultural Center

  Cultural Center At Rocky Neck

  9+ Interested
• Sat, 15 Nov, 2025 - 09:00 PM

  Bare Bones Boston at Drift

  DRIFT Gloucester

  9+ Interested
• Sat, 15 Nov, 2025 - 04:00 PM

  Past Life Regression & Angelic Message

  3A Pond Road, Gloucester, MA, United States, Massachusetts 01930

  4+ Interested
• Fri, 14 Nov, 2025 - 06:00 PM

  Pair of Cardinals Paint Party with Paula!

  Magnolia

  4+ Interested
• Fri, 12 Dec, 2025 - 06:00 PM

  Private event- DJ holiday party

  Beauport Hotel Gloucester

  9+ Interested
• Sat, 29 Nov, 2025 - 06:00 PM

  Vikings Alumni Hockey Game and Family Skate

  Talbot Rink

  7+ Interested
• Fri, 14 Nov, 2025 - 07:00 PM

  Cape Ann Shakespeare Troupe presents: Two Gentlemen of Verona by William Shakespeare

  Capt. Lester S. Wass American Legion Post 3

  12+ Interested
• Fri, 19 Dec, 2025 - 07:30 PM

  BrassFed Nation's Holiday Bash

  177 Main Street, Gloucester, MA, United States, Massachusetts 01930

  53+ Interested
• Fri, 21 Nov, 2025 - 06:00 PM

  Stress Reduction Workshop in the Salt Cave

  232 Main St

  USD 33
• Fri, 14 Nov, 2025 - 06:00 PM

  Silver Lining @ JD Meyers Magnolia Pub

  Jd & Meyers Best Friends

  30+ Interested
• Sun, 16 Nov, 2025 - 01:00 PM

  Beauport Boutique's Annual Sip & Shop

  55 Commercial St, Gloucester, MA, United States, Massachusetts 01930

  484+ Interested
• Sat, 15 Nov, 2025 - 10:00 AM

  Discover Saturdays

  Cape Ann Museum Green, 13 Poplar Street, Gloucester, MA
• Sat, 15 Nov, 2025 - 04:00 PM

  Horizon at Blue Collar Lobster 11/15

  Blue Collar Lobster Co.

  33+ Interested
• Sat, 20 Dec, 2025 - 08:30 PM

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

  The Rhumb Line
• Sat, 15 Nov, 2025 - 08:00 PM

  Once An Outlaw with The Peacheaters

  The Cut Live

  47+ Interested
• Sat, 29 Nov, 2025 - 12:00 AM

  Village Hall Dancing

  Brimpsfield Village Hall GL4 8LD
• Fri, 14 Nov, 2025 - 05:00 PM

  Live Music with Matt Rich

  75 Essex Ave (Rt. 133), Gloucester, MA, United States, Massachusetts 01930
• Sat, 22 Nov, 2025 - 04:00 PM

  Bordellos At The Blue Collar Lobster Co. Cafe!!

  Blue Collar Lobster Co.

  13+ Interested
• Thu, 13 Nov, 2025 - 06:00 PM

  Masshole Walking Group

  137 Main St, Gloucester, MA, United States, Massachusetts 01930
• Sat, 27 Dec, 2025 - 06:30 PM

  Elemental Balancing Experience in the Salt Cave

  Gloucester Massahusetts
• Sat, 17 Jan, 2026 - 08:00 PM

  LIVE from the LOUNGE - INGE BERGE

  Capt. Lester S. Wass American Legion Post 3
• Fri, 21 Nov, 2025 - 07:00 PM

  Livin' On Luck at Salted Cod, Gloucester

  53 Rocky Neck Ave

  Free
• Fri, 19 Dec, 2025 - 06:30 PM

  Holiday Drag Bingo

  1 Lexington Ave, Gloucester, MA, United States, Massachusetts 01930

  13+ Interested
• Sat, 15 Nov, 2025 - 09:00 AM

  Masshole & Co Pet Provisions Turns 1!

  137 Main St, Gloucester, MA, United States, Massachusetts 01930

  7+ Interested
• Wed, 19 Nov, 2025 - 06:15 PM

  Business After Hours at GMGI

  Gloucester Marine Genomics Institute, Inc.

  12+ Interested
• Sat, 06 Dec, 2025 - 08:00 PM

  Beck-Ola - Celebrating the Music of Jeff Beck, featuring Johnny A.

  The Cut Live

  9+ Interested
• Thu, 13 Nov, 2025 - 05:00 PM

  38th Annual Greater Cape Ann Chamber Auction - All Hands On Deck

  Cruiseport Gloucester

  22+ Interested
• Fri, 21 Nov, 2025 - 08:00 PM

  FJ - A Tribute To Foreigner & Journey

  The Cut Live

  20+ Interested
• Sun, 16 Nov, 2025 - 03:30 PM

  O'Brien's OBoru @ Blue Collar Lobster

  Blue Collar Lobster Co.

  42+ Interested
• Fri, 30 Jan, 2026 - 08:00 PM

  The Super 70s Rock Show

  177 Main Street, Gloucester, MA, United States, Massachusetts 01930

  9+ Interested
• Sun, 16 Nov, 2025 - 10:00 AM

  Annual Veterans Day Tournament!

  Harbor 9 Golf

  6+ Interested
• Sun, 16 Nov, 2025 - 03:00 PM

  A Conversation for Book Lovers

  1 Lexington Ave, Gloucester, MA
• Sun, 16 Nov, 2025 - 05:00 PM

  D&D at Hammond Castle Museum

  80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930

  60+ Interested
• Thu, 20 Nov, 2025 - 05:00 PM

  Film Screening & Panel Discussion: Timeline Cape Ann: Sawyer Free Library

  Sawyer Free Library

  6+ Interested
• Sat, 06 Dec, 2025 - 11:00 AM

  Bowl with Santa

  53 Gloucester Ave, Gloucester, MA, United States, Massachusetts 01930

  36+ Interested
• Sat, 22 Nov, 2025 - 06:00 PM

  Holiday Wreath Making

  232 Main Street, Gloucester, MA, United States, Massachusetts 01930

  13+ Interested
• Sat, 13 Dec, 2025 - 06:00 PM

  Welcome Yule! - Gloucester, MA

  Cultural Center At Rocky Neck

  22+ Interested
• Sat, 22 Nov, 2025 - 07:00 PM

  LIVE FROM THE LOUNGE - ToniAnn Enes

  8 Washington St, Gloucester, MA 01930-5734, United States

  6+ Interested
• Sat, 29 Nov, 2025 - 10:00 AM

  Holiday Sip and Shop

  Cruiseport Gloucester

  254+ Interested
• Thu, 04 Dec, 2025 - 05:00 PM

  Tip A Cop @ Minglewood Harborside

  Minglewood Tavern

  14+ Interested
• Fri, 14 Nov, 2025 - 07:00 PM

  Fridays

  CORE Peer Recovery & Resource Center
• Sat, 06 Dec, 2025 - 07:00 PM

  Beck-Ola

  The Cut Live

  25+ Interested
• Wed, 10 Dec, 2025 - 06:00 PM

  FUNdraiser: Holiday Door Swag Workshop

  103 R Maplewood Ave, Gloucester, MA, United States, Massachusetts 01930

  8+ Interested
• Sun, 30 Nov, 2025 - 11:00 AM

  Minglewood Marketplace

  25 Rogers St Gloucester, MA

  9+ Interested
• Sun, 30 Nov, 2025 - 10:30 AM

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

  Hammond Castle

  5+ Interested
• Sat, 29 Nov, 2025 - 10:00 AM

  Fourth Annual Gloucester Fishtown Horribles Parade of Trees

  First Baptist Church

  289+ Interested
• Tue, 25 Nov, 2025 - 05:00 PM

  Indoor golf tourney for Gloucester little league!

  Harbor 9 Golf

  6+ Interested
• Thu, 13 Nov, 2025 - 07:30 PM

  Danielia Cotton with Megan Wolffe

  The Cut Live

  12+ Interested
• Fri, 22 May, 2026 - 07:00 PM

  2026 Endless Night Vampire Salon: HAMMOND CASTLE

  Hammond Castle Museum

  USD 49
• Fri, 14 Nov, 2025 - 06:00 PM

  Sound Healing Bath in Salt Cave

  Revive Wellness

  USD 61
• Sat, 06 Dec, 2025 - 07:00 PM

  A Holiday Evening with Chelsea Berry

  80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930

  35+ Interested
• Sun, 07 Dec, 2025 - 03:00 PM

  Cookie Swap

  232 Main St

  USD 13
• Fri, 28 Nov, 2025 - 08:00 PM

  Rhythm of The Saints Tribute to Paul Simon with Special Guest Gary Backstrom Band

  The Cut Live

  57+ Interested
• Sat, 29 Nov, 2025 - 04:00 PM

  Annual Winter Wreath Workshop

  Magnolia Library and Community Center

  43+ Interested
• Sun, 16 Nov, 2025 - 03:30 PM

  JOIN US! Lecture next Sunday, Nov. 16th! Grand Hotels: The Hesperus & The Oceanside

  46 Magnolia Ave, Magnolia, MA, United States, Massachusetts 01930

  22+ Interested
• Thu, 04 Dec, 2025 - 05:30 PM

  Deck the Halls by Candlelight at Hammond Castle Museum

  80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930

  51+ Interested
• Thu, 20 Nov, 2025 - 05:00 PM

  Live Music with Peter Tentido

  75 Essex Ave (Rt. 133), Gloucester, MA, United States, Massachusetts 01930
• Wed, 26 Nov, 2025 - 09:00 PM

  Neon 90’s Thanksgiving Eve at Minglewood

  Minglewood Harborside

  194+ Interested
• Thu, 11 Dec, 2025 - 07:00 PM

  Holiday Wreath Making Class with Meredith McCarthy

  Beauport Hotel Gloucester

  USD 93
• Thu, 20 Nov, 2025 - 06:00 PM

  Trusted Adult North Shore for Parents & Caregivers

  Cape Ann YMCA

  6+ Interested
• Sat, 22 Nov, 2025 - 09:00 AM

  Holiday Craft Fair

  West Gloucester

  71+ Interested
• Sat, 18 Jul, 2026 - 08:00 PM

  AD/HD @ Minglewood Harborside!

  Minglewood Harborside

  30+ Interested
• Sat, 13 Dec, 2025 - 09:00 AM

  East Veterans Holiday Craft Fair

  Veterans Memorial

  175+ Interested
• Fri, 12 Dec, 2025 - 06:00 PM

  Shamanic Breathwork & Drum Circle

  232 Main St

  USD 54
• Sat, 06 Dec, 2025 - 08:00 AM

  Christmas Fair 2025

  Annisquam
• Sat, 13 Dec, 2025 - 11:00 AM

  Middle Street Walking Tours led by CAM Docents

  27 Pleasant St, Gloucester, MA, United States, Massachusetts 01930

  8+ Interested
• Mon, 17 Nov, 2025 - 12:00 PM

  Book presentation + signing with Katie Parla

  Pastaio Via Corta

  Free
• Sat, 27 Dec, 2025 - 06:00 PM

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

  The Cut Live

  42+ Interested
• Tue, 18 Nov, 2025 - 09:00 AM

  Gloucester Gratis Days: Complimentary Self-Guided Tours for Gloucester Residents

  80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930
• Fri, 05 Dec, 2025 - 05:15 AM

  FRIDAY 90s

  186 Main St, Gloucester, MA
• Sun, 07 Dec, 2025 - 04:00 PM

  Santa at the MLCC

  1 Lexington Ave, Gloucester, MA, United States, Massachusetts 01930

  94+ Interested
• Sat, 07 Mar, 2026 - 08:00 PM

  Nirvani - A Nirvana Tribute Experience with Foo!

  177 Main Street, Gloucester, MA, United States, Massachusetts 01930

  13+ Interested
• Tue, 25 Nov, 2025 - 09:00 AM

  Gloucester Gratis Days During Deck the Halls at Hammond Castle Museum

  80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930

  40+ Interested
• Sat, 24 Jan, 2026 - 10:00 AM

  5th Annual Gloucester’s So Salty

  27 Pleasant St, Gloucester, MA, United States, Massachusetts 01930

  56+ Interested
• Sun, 16 Nov, 2025 - 10:00 AM

  Holiday Mocktail Night

  232 Main Street, Gloucester, MA, United States, Massachusetts 01930

  17+ Interested
• Sat, 20 Dec, 2025 - 01:00 PM

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

  Capt. Lester S. Wass American Legion Post 3

  26+ Interested
• Sat, 10 Jan, 2026 - 03:00 PM

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

  Cape Ann Museum Green, 13 Poplar Street, Gloucester, MA

  8+ Interested
• Thu, 04 Dec, 2025 - 10:30 AM

  Coffee & Conversations: Gabrielle de Veaux Clements

  Cape Ann Museum Green, 13 Poplar Street, Gloucester, MA
• Sat, 06 Dec, 2025 - 10:00 AM

  Gloucester Elks Craft Fair - Sip n Shop

  Gloucester MA Elks Lodge #892

  127+ Interested
• Fri, 14 Nov, 2025 - 08:00 PM

  KARAOKE EVERY FRIDAY - in the Lounge

  8 Washington St, Gloucester, MA 01930-5734, United States
• Fri, 05 Dec, 2025 - 08:00 PM

  The Berklee College of Music Bob Marley Ensemble, directed by Matt Jenson

  The Cut Live

  14+ Interested
• Wed, 24 Dec, 2025 - 03:00 PM

  Christmas at the Magee's

  5 forest street Gloucester ma

  6+ Interested
• Thu, 20 Nov, 2025 - 07:00 PM

  LIVE! at The CUT

  The Cut Live

  104+ Interested