Must-Attend Events in Gloucester this Winter

January 04, 2023 / Things to Do & See

Most travelers think of Gloucester, Massachusetts as a summer destination filled with soft sand beaches, activities, and events on the water from spring through the fall. While this may be true, many don’t realize that Gloucester is alive with events long after the sun-drenched beaches clear out. From concerts and museums to art seminars and even some unique cultural festivals, Gloucester and Cape Ann are active all winter long. 

Even as many New Englanders start to cozy up next to a warm fire in the comfort of their living room, it’s worth venturing out to some of these events, festivals, and activities throughout Cape Ann this winter.

Gloucester’s So Salty 

The 2nd Annual Gloucester’s So Salty Festival begins on Saturday, January, 21st, and runs through the weekend with events scheduled from 10 am – 5 pm each day. The goal of this festival is to celebrate Gloucester’s uniquely “salty character” with local cultural institutions and businesses. 

Events and activities include viewing ice sculptures around the city, listening to live music, taking part in art activities, and enjoying salty treats throughout Downtown Gloucester and at the Cape Ann Museum. Admission to the festival is free and a full schedule of events can be found here. 

Kick-Off Events to Celebrate Gloucester’s 400th Anniversary

This year marks the 400th anniversary of the founding of Gloucester, Massachusetts. To commemorate this significant milestone, Gloucester Celebrations Corporation (GCC) is sponsoring a year-long celebration of Gloucester through special events found on their site called Gloucester 400+™.

To mark the commencement of the fifth century of incorporation, Gloucester will be hosting concerts, art events, cultural events, and some “uniquely Gloucester events. These include the New Year’s Day Polar Plunge on the first of the year, First Friday Art After Hours at Cape Ann Museum on January 6th, and Overture to 2023, which is a program of music, dance, poetry, photography, and speakers to kick off the celebrations on January 15th. 

Musical Performances & Art Exhibitions

Gloucester is a city rich with culture including performances of live music of multiple styles as well as art exhibitions across town, and more specifically at Rocky Neck Art Colony. 

For music lovers, we invite you to take a look at the live musical performance calendar at the Shalin Liu Performance Center of Rockport Music. There you will find a comprehensive list of their shows and performances including classical, jazz, folk, pop, and world music, as well as a film series and HD broadcasts from the Metropolitan Opera and England’s National Theatre. 

Many restaurants on Cape Ann also offer live music year-round. Minglewood Harborside provides both live music and trivia for its guests to enjoy. Not only can you savor waterfront dining with scrumptious local foods, but be entertained by local and regional musicians even throughout the winter!

In addition to live music, Gloucester also has a thriving art community with workshops and exhibits at Rocky Neck Art Colony. A full calendar of exhibits including seminars, drawing classes, yoga classes, and pottery lessons is available on their site. Visiting the area allows for a view of the world of art as well as the scenic views along Gloucester’s harbor. 

If you’re heading to Cape Ann this winter check out Discover Gloucester’s comprehensive list of hotels, accommodations, and bed and breakfasts so you can make a weekend of enjoying all this region can offer – even deep into winter!