All Upcoming events

• Sat, 28 Feb, 2026 - 06:00 PM

  Bridgerton Ball

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

  146+ Interested
• Sat, 07 Feb, 2026 - 08:00 PM

  Back to Black LIVE: An Amy Winehouse Tribute Starring Megan Wolffe

  The Cut Live

  42+ Interested
• Fri, 06 Feb, 2026 - 08:00 PM

  Little Lies - A Tribute to Fleetwood Mac

  The Cut Live

  70+ Interested
• Sat, 04 Apr, 2026 - 08:00 PM

  Fast Times

  The Cut Live

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

  2026 Endless Night Vampire Salon: HAMMOND CASTLE

  Hammond Castle Museum

  USD 49
• Sun, 08 Feb, 2026 - 07:00 PM

  Super Bowl Party

  The Cut Live

  9+ Interested
• Fri, 20 Mar, 2026 - 08:00 PM

  Altan

  The Cut Live

  16+ Interested
• Sat, 07 Feb, 2026 - 07:30 PM

  Annisquam Village Players Winter Cabaret 2026

  The historic Annisquam Village Hall, 36 Leonard St., Gloucester, MA

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

  Nirvani - A Nirvana Tribute Experience with Foo!

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

  37+ Interested
• Sat, 07 Mar, 2026 - 11:00 AM

  Mad Science at the Castle

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

  26+ Interested
• Sun, 08 Mar, 2026 - 06:30 PM

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

  The Cut Live

  18+ Interested
• Fri, 20 Feb, 2026 - 08:30 PM

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

  The Rhumb Line
• Sat, 28 Feb, 2026 - 07:00 PM

  Left Right Center Tournament

  The Elks at Bass Rocks

  70+ Interested
• Mon, 16 Feb, 2026 - 09:00 AM

  Kids' Free Week During School Vacation Week

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

  129+ Interested
• Fri, 06 Mar, 2026 - 08:00 PM

  Dueling Pianos

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

  20+ Interested
• Fri, 13 Feb, 2026 - 07:30 PM

  Mardi Gras with the Jambalaya Horns

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

  17+ Interested
• Sun, 06 Dec, 2026 - 09:00 AM

  Happy Holidays Half MerryThon & 5K

  Good Harbor Beach
• Sun, 29 Mar, 2026 - 06:00 PM

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

  Floating Lotus Gloucester

  8+ Interested
• Sat, 14 Feb, 2026 - 08:00 PM

  Don't Stop Believin, Live Band Karaoke Showcase with Groove Therapy - hosted by DJ Lou

  The Cut Live

  31+ Interested
• Sat, 14 Mar, 2026 - 08:30 PM

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

  The Rhumb Line

  73+ Interested
• Fri, 20 Feb, 2026 - 09:00 PM

  Bob Marley night

  Minglewood Harborside

  70+ Interested
• Fri, 13 Feb, 2026 - 07:00 PM

  Livin' On Luck at Salted Cod

  Salted Cod Arthouse & Wine Bar

  Free
• Sun, 15 Feb, 2026 - 11:30 AM

  Sunday Jazz Brunch - On the Water.

  75 Essex Ave (Rt. 133), Gloucester, MA, United States, Massachusetts 01930

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

  AD/HD @ Minglewood Harborside!

  Minglewood Harborside

  30+ Interested
• Sat, 21 Mar, 2026 - 07:30 PM

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

  The Cut Live
• Sat, 28 Feb, 2026 - 01:00 PM

  Bridgerton Afternoon Tea at the Castle

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

  306+ Interested
• Thu, 05 Feb, 2026 - 08:00 PM

  Terrafunk & The Rupert Selection

  The Cut Live

  55+ Interested
• Sat, 04 Apr, 2026 - 09:00 PM

  Chosen one album release party

  Minglewood Harborside

  4+ Interested
• Sat, 21 Feb, 2026 - 07:00 PM

  Veuve "Clicquot in the Snow" 2026

  Beauport Hotel Gloucester

  USD 13
• Thu, 05 Feb, 2026 - 05:30 PM

  2nd Annual Driving for Dollars Virtual Golf Charity Event

  Harbor 9 Golf

  10+ Interested
• Thu, 26 Mar, 2026 - 08:00 PM

  The Cold Stares

  The Cut Live

  6+ Interested
• Sat, 28 Mar, 2026 - 10:00 PM

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

  Gloucester Unitarian Universalist Church
• Fri, 03 Apr, 2026 - 09:00 PM

  Allegra and the Daydreamers at Drift

  DRIFT Gloucester

  6+ Interested
• Thu, 05 Feb, 2026 - 05:30 PM

  Yin Yoga & Yin Magic

  6 Lexington Ave., Magnolia, MA, United States, Massachusetts 01930
• Sat, 14 Mar, 2026 - 08:00 PM

  Neon 90’s at The Cut

  The Cut Live

  66+ Interested
• Tue, 03 Mar, 2026 - 05:00 PM

  Purim Celebration & Grand Hamantash Bake

  37 Main Street, Gloucester, MA, United States, Massachusetts 01930
• Fri, 06 Mar, 2026 - 04:00 PM

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

  Beauport Hotel Gloucester

  USD 375
• Mon, 16 Feb, 2026 - 09:00 AM

  February Vacation at Art Haven: Grades K-5th

  20 Maplewood Ave, Unit 3, Gloucester, MA, United States, Massachusetts 01930
• Sat, 28 Feb, 2026 - 07:00 PM

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

  5 Short Street , Gloucester, MA, United States, Massachusetts 01930

  49+ Interested
• Sat, 07 Feb, 2026 - 11:00 AM

  Oceans of Love at Beauport Hotel

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

  133+ Interested
• Thu, 05 Feb, 2026 - 06:00 PM

  Piano Bar at Beauport Hotel

  55 Commercial St, Gloucester, MA, United States, Massachusetts 01930
• Sat, 07 Mar, 2026 - 09:30 AM

  Spring Seed Giveaway

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

  5+ Interested
• Sun, 01 Mar, 2026 - 12:00 PM

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

  The Cut Live

  31+ Interested
• Sun, 22 Feb, 2026 - 11:30 AM

  Veuve Clicquot Brunch by the Sea

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

  10+ Interested
• Tue, 03 Feb, 2026 - 06:00 PM

  Live Music Tuesdays

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