Gloucester Christmas Events

Holiday Wreath Making Course

Apothecary Suil Crow 15 Nov 2026

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

Hammond Castle Museum 5 Dec 2026

Holiday Wreath Making Class with Meredith McCarthy

Beauport Hotel Gloucester 3 Dec 2026

Happy Holidays Half MerryThon & 5K

Good Harbor Beach 6 Dec 2026

Cape Ann Artisans & North Shore Arts Association Holiday Market

North Shore Art Association 6 Nov 2026

Holiday Sip and Shop at Cruiseport

Cruiseport Gloucester 29 Nov 2026

Holidays and Wintertide

The Cut Live 12 Dec 2026

5th Annual Parade of Trees

First Baptist Church 4 Dec 2026

Middle Street Walking Tour

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

Bowl with Santa

53 Gloucester Ave, Gloucester, MA, United States, Massachusetts 01930 12 Dec 2026

Ladies Night

242 Main St, Gloucester, MA 3 Dec 2026

NUESE Gloucester Christmas Concert

70 Middle St, Gloucester, MA 01930-5739, United States 12 Dec 2026

Last Minute Holiday Market at The Cut!

177 Main St, Gloucester, MA 01930-5703, United States 19 Dec 2026

Winter Wonderland Candle

Apothecary Suil Crow 8 Nov 2026