Holiday events in Gloucester in December

• Sat, 13 Dec, 2025 - 08:00 PM

  HOLIDAYS & WINTERTIDE A night of Christmas and Winter Music

  The Cut Live

  36+ Interested
• Sun, 07 Dec, 2025 - 05:30 PM

  A Holiday Evening with Chelsea Berry

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

  62+ Interested
• Sun, 07 Dec, 2025 - 09:00 AM

  Deck the Halls at Hammond Castle Museum

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

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

  `14th Annual Spruce Road Extravaganza

  Blue Collar Lobster Company

  USD 100
• Sun, 07 Dec, 2025 - 09:00 AM

  Happy Holidays Half MerryThon & 5K

  Good Harbor Beach
• Sat, 20 Dec, 2025 - 08:30 PM

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

  The Rhumb Line
• Sat, 06 Dec, 2025 - 09:00 AM

  Holiday Market at Second Glance

  2 Pond Rd, Gloucester, MA, United States, Massachusetts 01930

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

  Holiday Wreath Making Class with Meredith McCarthy

  Beauport Hotel Gloucester

  USD 93
• Sat, 20 Dec, 2025 - 12:00 PM

  Holiday Sip & Shop Open House

  Lighthouse Marina

  89+ 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

  65+ Interested
• Wed, 10 Dec, 2025 - 06:30 PM

  Holiday Craft Night: Sea Glass Christmas Tree Making

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

  12+ Interested
• Thu, 11 Dec, 2025 - 10:00 AM

  Men's Day

  Downtown Gloucester