Happening Next

Gloucester Holiday Events

Holiday events Happening Next in Gloucester, MA

Yule Candle Making Course

Apothecary Suil Crow 8 Nov 2026
WORKSHOPS

Holiday Wreath Making Course

 Apothecary Suil Crow 15 Nov 2026
WORKSHOPS

Beauport Boutique's Annual Sip & Shop

 55 Commercial St, Gloucester, MA, United States, Massachusetts 01930 15 Nov 2026
SHOPPING

Holiday Wreath Making Class with Meredith McCarthy

 Beauport Hotel Gloucester 3 Dec 2026
CHRISTMAS-WREATH-WORKSHOPS USD 93

Happy Holidays Half MerryThon & 5K

 Good Harbor Beach 6 Dec 2026
HOLIDAY

Gloucester Gratis Days: Free Admission for Gloucester Residents

 80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930 29 Sep 2026
ART

Cape Ann Artisans & North Shore Arts Association Holiday Market

 North Shore Art Association 6 Nov 2026
HOLIDAY FREE

Holiday Sip and Shop at Cruiseport

 Cruiseport Gloucester 29 Nov 2026
HOLIDAY

Tease The Season Burlesque Show

 The Cut Live 13 Dec 2026
PERFORMANCES

Holidays and Wintertide

 The Cut Live 12 Dec 2026
MUSIC

5th Annual Parade of Trees

First Baptist Church 4 Dec 2026
PARADES

Middle Street Walking Tour

 27 Pleasant St, Gloucester, MA, United States, Massachusetts 01930 12 Dec 2026
HOLIDAY

Family Craft Day: Magic in a Jar – Creating Your Own Holiday Snow Globe

 Apothecary Suil Crow 22 Nov 2026
HOLIDAY

Last Minute Holiday Market at The Cut!

 177 Main St, Gloucester, MA 01930-5703, United States 19 Dec 2026
CHRISTMAS-MARKETS-AND-FAIRS

Winter Wonderland Candle

Apothecary Suil Crow 8 Nov 2026
WORKSHOPS