Gloucester Holiday Events

Firebird Pops Orchestra Presents Christmas at the Castle

80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930 19 Dec 2025

BrassFed Nation's Holiday Bash

177 Main Street, Gloucester, MA, United States, Massachusetts 01930 19 Dec 2025

Holiday Drag Bingo

1 Lexington Ave, Gloucester, MA, United States, Massachusetts 01930 19 Dec 2025

F-BOMB PRE-XMAS PARTY

Minglewood Harborside 13 Dec 2025

Deck the Halls by Candlelight at Hammond Castle Museum

80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930 18 Dec 2025

Last Minute Holiday Market at The Cut!

177 E Main St, Gloucester, MA 01930-3801, United States 21 Dec 2025

`14th Annual Spruce Road Extravaganza

Blue Collar Lobster Company 20 Dec 2025

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

The Rhumb Line 20 Dec 2025

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

Capt. Lester S. Wass American Legion Post 3 20 Dec 2025

Holiday Sip & Shop Open House

Lighthouse Marina 20 Dec 2025

December 17th: Jingle Bar at Beauport Hotel

Beauport Hotel Gloucester 17 Dec 2025

Marshalls farmstand holiday fair

Marshall's Farm Stand & Greenhouses 14 Dec 2025

December 22nd: Jingle Bar at Beauport Hotel

Beauport Hotel Gloucester 22 Dec 2025

2026 Endless Night Vampire Salon: HAMMOND CASTLE

Hammond Castle Museum 22 May 2026

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

UCC Magnolia 3 Norman Ave, Magnolia, MA 14 Dec 2025