All Upcoming events

• Fri, 19 Dec, 2025 - 05:30 PM

  Firebird Pops Orchestra Presents Christmas at the Castle

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

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

  BrassFed Nation's Holiday Bash

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

  63+ Interested
• Fri, 02 Jan, 2026 - 07:30 PM

  Cape Ann Big Band New Year’s Concert

  10 Church St, Gloucester, MA, United States, Massachusetts 01930
• Sat, 20 Dec, 2025 - 09:00 PM

  Less Than Zero @ DRIFT Gloucester

  DRIFT Gloucester
• Fri, 19 Dec, 2025 - 06:00 PM

  108 Sun Salutations

  186 Main St, Gloucester, MA
• Fri, 19 Dec, 2025 - 06:30 PM

  Holiday Drag Bingo

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

  30+ Interested
• Sat, 27 Dec, 2025 - 06:30 PM

  Elemental Balancing Experience in the Salt Cave

  232 Main Street, Gloucester, MA, United States, Massachusetts 01930
• Sat, 20 Dec, 2025 - 06:30 PM

  An Enchanting Evening of Winter Solstice; Ritual & Mediumship in the Salt Cave

  232 Main Street, Gloucester, MA, United States, Massachusetts 01930
• Sat, 27 Dec, 2025 - 05:30 PM

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

  The Cut Live

  66+ Interested
• Sat, 20 Dec, 2025 - 06:30 PM

  An Enchanted Evening of Winter Solstice Ritual & Mediumship

  232 Main St

  USD 55
• Fri, 16 Jan, 2026 - 07:30 PM

  A Special Film Screening: TOWNIE, Starring Steve Sweeney

  The Cut Live
• Sat, 20 Dec, 2025 - 10:00 AM

  Discover Saturdays

  Cape Ann Museum Green, 13 Poplar Street, Gloucester, MA
• Fri, 19 Dec, 2025 - 06:30 PM

  An Enchanting Evening of Winter Solstice Ritual & Mediumship

  232 Main St

  USD 55
• Fri, 16 Jan, 2026 - 06:00 PM

  Sound Healing Bath in the Salt Cave

  232 Main Street, Gloucester, MA, United States, Massachusetts 01930
• Thu, 18 Dec, 2025 - 05:30 PM

  Deck the Halls by Candlelight at Hammond Castle Museum

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

  16+ Interested
• Fri, 19 Dec, 2025 - 05:00 PM

  Live Music with Matt Rich

  75 Essex Ave (Rt. 133), Gloucester, MA, United States, Massachusetts 01930
• Sat, 20 Dec, 2025 - 08:00 PM

  Acoustic View Bill Dwyer &Friends

  Snug Harbor Studio 39 Ye Olde County Rd Gloucester
• Fri, 13 Feb, 2026 - 07:00 PM

  Livin' On Luck at Salted Cod

  Salted Cod Arthouse & Wine Bar

  Free
• Sat, 20 Dec, 2025 - 10:30 AM

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

  Hammond Castle
• Sun, 21 Dec, 2025 - 12:00 PM

  Last Minute Holiday Market at The Cut!

  177 E Main St, Gloucester, MA 01930-3801, United States

  59+ Interested
• Sat, 31 Jan, 2026 - 07:00 PM

  LIVE FROM THE LOUNGE - ToniAnn Enes

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

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

  Nirvani - A Nirvana Tribute Experience with Foo!

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

  17+ Interested
• Sat, 17 Jan, 2026 - 08:00 PM

  Annie Brobst with Whiskey-6 & Ross Livermore

  The Cut Live

  109+ Interested
• Sat, 20 Dec, 2025 - 06:00 PM

  `14th Annual Spruce Road Extravaganza

  Blue Collar Lobster Company

  USD 100
• Tue, 16 Dec, 2025 - 07:30 PM

  Music Video Bingo in our Pub

  53 Gloucester Ave, Gloucester, MA, United States, Massachusetts 01930
• Sun, 08 Feb, 2026 - 07:00 PM

  Super Bowl Party

  The Cut Live

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

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

  The Rhumb Line
• Sat, 17 Jan, 2026 - 08:00 PM

  LIVE from the LOUNGE - INGE BERGE

  Capt. Lester S. Wass American Legion Post 3
• Sat, 27 Dec, 2025 - 06:30 PM

  Elemental Balancing Experience in the Salt Cave

  Gloucester Massahusetts
• Thu, 18 Dec, 2025 - 05:00 PM

  Live Music with Peter Tentido

  75 Essex Ave (Rt. 133), Gloucester, MA, United States, Massachusetts 01930
• Fri, 19 Dec, 2025 - 07:00 PM

  Fridays

  CORE Peer Recovery & Resource Center
• 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

  65+ Interested
• Sat, 17 Jan, 2026 - 07:00 PM

  Left Right Center Tournament

  The Elks at Bass Rocks

  46+ Interested
• Wed, 31 Dec, 2025 - 09:00 PM

  New Year’s Eve Bash at Minglewood Harborside

  Minglewood Harborside
• Sat, 20 Dec, 2025 - 12:00 PM

  Holiday Sip & Shop Open House

  Lighthouse Marina

  92+ Interested
• Thu, 15 Jan, 2026 - 07:00 PM

  Sister Circle: Aligning with Our Dream Life through a Month Off Booze

  232 Main Street, Gloucester, MA, United States, Massachusetts 01930
• Fri, 26 Dec, 2025 - 09:00 PM

  Eagle in the Attic at Minglewood 12/26

  Minglewood Harborside

  11+ Interested
• Fri, 23 Jan, 2026 - 08:00 PM

  Dead to the Core - January Show

  The Cut Live
• Fri, 06 Feb, 2026 - 08:00 PM

  Little Lies - A Tribute to Fleetwood Mac

  The Cut Live

  17+ Interested
• Wed, 17 Dec, 2025 - 06:00 PM

  December 17th: Jingle Bar at Beauport Hotel

  Beauport Hotel Gloucester
• Sat, 24 Jan, 2026 - 08:00 PM

  The Beautiful Losers - A Tribute to Bob Seger & The Silver Bullet Band

  The Cut Live

  6+ Interested
• Sun, 21 Dec, 2025 - 03:30 PM

  Peter Pan

  10 Church St, Gloucester, MA, United States, Massachusetts 01930
• Thu, 01 Jan, 2026 - 11:00 AM

  New Year's Day: Rhythm in Flow

  3A Pond Road, Gloucester, MA, United States, Massachusetts 01930
• Tue, 16 Dec, 2025 - 09:00 AM

  Deck the Halls at Hammond Castle Museum

  80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930
• Fri, 26 Dec, 2025 - 08:30 PM

  Muddy Ruckus at The Rhumb Line

  The Rhumb Line
• Sat, 24 Jan, 2026 - 10:00 AM

  5th Annual Gloucester’s So Salty

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

  202+ Interested
• Thu, 18 Dec, 2025 - 07:00 PM

  The Spynz - Third Thursday (music) Therapy FREE Show

  The Cut Live

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

  Mardi Gras with the Jambalaya Horns

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

  7+ Interested
• Thu, 18 Dec, 2025 - 06:00 PM

  Masshole Walking Group

  137 Main St, Gloucester, MA, United States, Massachusetts 01930
• Sat, 27 Dec, 2025 - 10:30 AM

  Plunge for Pete

  Bass Rocks, Gloucester, MA
• Fri, 30 Jan, 2026 - 08:00 PM

  The Super 70s Rock Show

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

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

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

  The Cut Live

  14+ Interested
• Wed, 31 Dec, 2025 - 07:30 PM

  SAFETY - THE NYE EXTRAVAGANZA - Late Show

  The Cut Live

  7+ Interested
• Wed, 31 Dec, 2025 - 07:30 PM

  Glitz & Glam NYE 2026 Party at Harbor 9

  Harbor 9 Golf & Sports Bar

  USD 29
• 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

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

  AD/HD @ Minglewood Harborside!

  Minglewood Harborside

  30+ Interested
• Mon, 22 Dec, 2025 - 06:00 PM

  December 22nd: Jingle Bar at Beauport Hotel

  Beauport Hotel Gloucester

  USD 18
• Fri, 26 Dec, 2025 - 09:00 AM

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

  20 Maplewood Ave, Unit 3, Gloucester, MA, United States, Massachusetts 01930
• Tue, 16 Dec, 2025 - 07:00 PM

  Wintersong: A Celtic Advent Meditation

  1123 Washington St, Gloucester, MA, United States, Massachusetts 01930

  10+ Interested
• Mon, 05 Jan, 2026 - 06:30 PM

  The Nectar Exchange

  6 Lexington Ave., Magnolia, MA, United States, Massachusetts 01930
• Sun, 21 Dec, 2025 - 01:00 PM

  CHRISTMAS KIDS PARTY @ AMERICAN LEGION POST 3!!!

  Capt. Lester S. Wass American Legion Post 3

  34+ Interested
• Sat, 10 Jan, 2026 - 01:00 PM

  Children & Family Workshop (Free) with Loren Doucette

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

  9+ 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

  7+ Interested
• Thu, 29 Jan, 2026 - 05:30 PM

  The Gloucesterman Adventure: Jonathan Bayliss and Schooner Adventure at 100

  Sawyer Free Library

  Free
• Sun, 21 Dec, 2025 - 02:00 PM

  Minglewood Winter Market

  Minglewood Harborside

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

  2026 Endless Night Vampire Salon: HAMMOND CASTLE

  Hammond Castle Museum

  USD 49
• Thu, 29 Jan, 2026 - 06:45 PM

  Scotty Austin - The Northeast Invasion Tour

  The Cut Live
• Fri, 20 Feb, 2026 - 08:30 PM

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

  The Rhumb Line
• Tue, 16 Dec, 2025 - 06:00 AM

  Lobster Trap Menorah Lighting

  Temple Ahavat Achim
• Fri, 20 Feb, 2026 - 09:00 PM

  Bob Marley night

  Minglewood Harborside

  32+ Interested
• Wed, 17 Jun, 2026 - 06:00 PM

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

  The Historic Ben Butler Homestead

  Free
• Tue, 16 Dec, 2025 - 09:00 AM

  Gloucester Gratis Days During Deck the Halls at Hammond Castle Museum

  80 Hesperus Ave, 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
• Sun, 21 Dec, 2025 - 05:30 PM

  Holidays With The Bordellos!!

  The Rhumb Line
• Fri, 10 Jul, 2026 - 09:00 PM

  Spike the Punch at Minglewood

  The Minglewod Gloucester MA

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

  Christmas at the Magee's

  5 forest street Gloucester ma

  9+ Interested
• Tue, 17 Feb, 2026 - 06:00 PM

  Jeff Fraser solo at the Beauport

  Beauport Hotel Gloucester
• Thu, 18 Dec, 2025 - 10:00 AM

  Shop Until 9 PM

  Main Street, Gloucester, MA, United States, Massachusetts 01930
• Thu, 01 Jan, 2026 - 05:30 PM

  Yin Yoga & Yin Magic

  6 Lexington Ave., Magnolia, MA, United States, Massachusetts 01930