Plan the Ultimate Gloucester, MA Winter Vacation

Winter is arguably one of the best times to plan a vacation in Gloucester, MA. There are several school breaks, the crowds are minimal, and the views are spectacular. From stunning snow-capped views to amazing off-season deals, Gloucester is a hidden winter gem.

A Luxurious Stay

The Beauport Hotel Gloucester 

If you want to save money and still feel like you’re living a life of luxury, you should book your stay at the Beauport Hotel in Gloucester. With great rates for the off-season, their rooms offer spacious elegance, coastal and city views, plush bedding, and modern comfort. There are also special seasonal deals and packages, including celebration packages, reduced rates for local theater and concert tickets during your stay, and deals for seniors.

The Harbobrview Inn

If you’re looking for a cozy weekend getaway, consider the Harborview Inn, located along Massachusetts’ oldest harbor. With stunning views and dazzling sunrises, the inn is just steps from Gloucester’s charming downtown. Begin your morning with a complimentary breakfast, spend the day discovering local shops and galleries, and end it relaxing by the fireplace overlooking the coast.

Private Art Studio Tours

Many of the incredible Cape Ann Artisans allow tours of their studios year-round, so long as you make an appointment. And why wouldn’t you? You’ll get a private tour of the studio and an amazing look at the artist’s works. There’s sculptures, pottery, paintings, jewelry, glass beads, weaving, and more to look over and even buy. It’s a great way to find unique holiday gifts for art-loving friends and family.

Dine on Fresh Seafood

In Massachusetts, there’s never a bad time of the year for seafood. This is even more true when you’re in a famous fishing port like Gloucester. Make plans for a sumptuous seafood dinner at one of Gloucester’s amazing restaurants. 

Gloucester House Pub 

From October through May Gloucester House Pub is open, featuring cozy indoor dining. They not only offer fresh, locally-sourced seafood and other tasty traditional dishes, but they were the first to popularize fried calamari and make it a New England favorite.

Mile Marker One Waterfront Restaurant 

Have you ever wanted to dine in an igloo? Well, at Mile Marker One Waterfront Restaurant, you can, and a heated one at that! The clear igloos are available outdoors on the deck, allowing you to experience the ocean views while still remaining cozy. And while the weather outside is frozen, the seafood never is, being locally-sourced and fresh off the boat to your table.

1606 Oyster Bar 

With panoramic ocean views, 1606 Restaurant & Bar lets you enjoy the coastal beauty of Gloucester without stepping into the cold. Located in the lobby of the Beauport Hotel, it’s the perfect spot to sip inventive cocktails and indulge in a delicious meal. From fresh-caught fish and signature seafood towers to comforting dishes with a modern twist, there is something for everyone’s palate.

Holiday Castle by the Sea

Hammond Castle was the home of inventor John Hays Hammond, Jr., and his home reflects his eccentric personality. A medieval-style castle filled with Roman, Renaissance, and medieval artifacts as well as exhibits showcasing Hammond’s life and inventions, it’s always a treat to visit.

While the museum is closed to tours January through the end of March to , it remains open in November through mid-December, Friday through Sunday, then open daily until the end of the year. There are also special events you can attend in February & March. What makes the museum notable during this time is that rooms are elegantly decorated for the holiday season during this time by local designers.

Winter Hikes

If you love snowy walks or cross-country skiing, Ravenswood Park is the perfect place for outdoor winter adventures. Enjoy the peaceful beauty of the 600-acre property as you search for animal tracks, make snowmen, and explore the snowy wilderness. Be sure to bundle up!

When winter comes around, don’t fool yourself into believing you need to stay home. Book a trip to Gloucester and prepare yourself for fun, food, and luxurious stays.