5 Things To Do In Gloucester During the Winter 

December 05, 2023 / Things to Do & See

While you may associate Gloucester with beaches, sailing and the bustling harbor during the peak of the summer season, it is also a perfect destination to enjoy a winter weekend exploring all the city has to offer. From concerts and shows to art and culture in local museums, there is so much to see and do even during the coldest days of the winter. 

Here are just five ideas to inspire your next wintery visit to Gloucester and Cape Ann. 

Winter Birding

Did you know that Gloucester and Cape Ann are home to rare bird species? In the winter, the highly anticipated Harlequin Ducks grace our waters, and are especially visible at Halibut Point State Park, on the edge of Cape Ann. The DCR team at Halibut Point offer weekly birding walks around their trails network to locals and visitors seeking to peep these special creatures. You may even spot a snowy owl if you’re lucky! Other great spots to catch glimpses of coastal fowl this winter include Eastern Point Lighthouse, Greenbelt’s Seine Field and Bass Rocks properties, the rocky coastline of Rockport, and ofcourse, Gloucester’s beautiful beaches.

Enjoy Theater & Musical Performances 

Gloucester Stage Company located on East Main Street is a professional non-profit theater company that presents contemporary plays and rousing classics that have moved on to commercial productions in New York and Paris.

Located in a century-old brick warehouse on the Gloucester oceanfront, the unique three-quarter thrust stage provides an intimate experience for audiences. Recent performances and events included Tall Tales from Blackburn Tavern, the critically acclaimed Private Lives, Ding Dongs, STEW, a free film series featuring Little Women, The Fantastic Mr. Fox, and their annual Home For the Holidays special, as well as live performances of Henri Smith’s New Orleans Holiday Special. 

For a complete schedule of performances visit Gloucester Stage Company Calendar of Events. 

For those who love music, whether it is classical, jazz, folk, or pop, the Shalin Liu Performance Center in Rockport, Massachusetts is just the place for you to take in a concert. The beautiful concert hall overlooks the Atlantic Ocean on the coast of Rockport. Check out their comprehensive schedule this winter and plan a trip to visit Cape Ann in the coming weeks. 

New to Gloucester this winter is The Cut! The Cut is a multi-purpose entertainment venue named after an iconic bridge. Coming soon to Gloucester, Massachusetts. Designed by musicians. Inspired by community. Shows start in early 2024, with their 180-seat restaurant open now!

Visit A Museum 

In the spring and summer months, visitors flock to the beaches and the coastline activities only to wish they had more time to explore the history and museums of Cape Ann. The winter is the perfect time to move indoors to enjoy places like the Cape Ann Museum, Maritime Gloucester Museum, or the unique architecture of the Hammond Castle Museum.

Whether you enjoy maritime history, American art and culture, or a one-of-a-kind collection of artifacts, you will be inspired and entranced by the exhibits and workshops available in Gloucester’s museums and galleries. Check out the full calendar at each museum to plan your trip and learn more about this quintessential New England area. 

Shop & Dine 

Gloucester’s downtown shopping and dining district is a wonderful place to visit in the winter. Shops offer goods from local craftspeople that make for perfect gifts for anniversaries, birthdays, and “just because.” 

While you are strolling and shopping, don’t forget to taste some of the amazing cuisine options Gloucester has to offer. From Thai and Portuguese fares to delicious Italian and Lebanese options, and delectable seafood dishes offered in heated Igloos at Mile Marker One, a variety of enticing restaurants line the main streets of Gloucester and promise that you won’t go home hungry. In fact, you’ll be planning your next visit! 

Gloucester isn’t just a destination during the spring and summer months, it’s a wonderful place to spend the day exploring, take a winter weekend getaway, or just enjoy the afternoon shopping and tasting your way through the many shops and dining establishments! Start to dream up your perfect foodie getaway along the Gloucester Seaport Trail.

Take Your Pup For A Beach Walk 

Wintertime is the perfect season to enjoy the solitude of Gloucester’s many beaches. It’s also a time when dogs are allowed to romp, run and play on the sand while their owners enjoy the stunning views. 

While the beaches are reserved for human visitors during the spring and summer months, from late fall to early spring, canine companions are allowed on the beaches. Good Harbor, Wingaersheek, Cressy’s, and Plum Cove beaches are amazing places to take your fur friend for some exercise or socialization outdoors. From sniffing and exploring the rocks to playing with other canines, it’s a great way to spend a brisk winter day.