Gloucester Holiday Events

HOLIDAYS & WINTERTIDE A night of Christmas and Winter Music

The Cut Live 13 Dec 2025

Private event- DJ holiday party

Beauport Hotel Gloucester 12 Dec 2025

BrassFed Nation's Holiday Bash

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

Holiday Sip and Shop

Cruiseport Gloucester 29 Nov 2025

Holiday Craft Night: Wooden Gnome Decorating

Revive Wellness 7 Nov 2025

Beauport Boutique's Annual Sip & Shop

55 Commercial St, Gloucester, MA, United States, Massachusetts 01930 16 Nov 2025

Holiday Wreath Making

232 Main Street, Gloucester, MA, United States, Massachusetts 01930 22 Nov 2025

Paint Your Own Mini Ceramic Buoy Ornament

20 Maplewood Ave, Unit 3, Gloucester, MA, United States, Massachusetts 01930 7 Nov 2025

Fourth Annual Gloucester Fishtown Horribles Parade of Trees

First Baptist Church 29 Nov 2025

A Holiday Evening with Chelsea Berry

80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930 7 Dec 2025

Holiday Wreath Making Class with Meredith McCarthy

Beauport Hotel Gloucester 11 Dec 2025

East Veterans Holiday Craft Fair

Veterans Memorial 13 Dec 2025

Holiday Craft Fair

West Gloucester 22 Nov 2025

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

80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930 11 Nov 2025

Holiday Mocktail Night

Revive Wellness 16 Nov 2025

Holiday Mocktail Night

232 Main Street, Gloucester, MA, United States, Massachusetts 01930 24 Nov 2025

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

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

Gloucester Elks Craft Fair - Sip n Shop

Gloucester MA Elks Lodge #892 6 Dec 2025