12 Best Towns in Massachusetts for a Winter Getaway
The cold and chilly winter should not stop you from visiting this state. Massachusetts, officially known as the Commonwealth of Massachusetts, is a historic state in the New England region, famous for the role it played in the American Revolution.
It is bordered to the east and southeast by the Atlantic Ocean and the Gulf of Maine, making Massachusetts a perfect bay state. Winter is the perfect time to visit the Bay State, from walking along the bayside without the usual summer rush to snowboarding down the slopes at the Wachusett mountains, taking in every inch of the breathtaking surroundings.
These are some of the best towns in Massachusetts for a winter getaway with your friends, family, or significant other. Pack your bags and prepare for an adventure in these towns.
Concord
Concord is a small town in Middlesex County along the Concord River. This town is small and old-fashioned, with well-preserved historic buildings. Concord is one of the two towns that had the honor of opening the military phase of the American Revolution.
In winter, this historic town becomes a perfect snow-globe town. Learn more about Concord's history from your visit to the Concord Museum. This museum has a lot of artifacts from the early settlers in this area and some personal belongings of great literary artists from this town.
Walden Pond State Reservation is open to people all year round. Wear comfortable shoes and cold fighting outfits in winter to go hiking up the several trails in this reservation area. On your hike, visit the spot where Thoreau lived and wrote between 1845 and 1847. Stay at Concord's Colonial Inn. This 17th-century Inn is a magical place, especially during the festive periods.
Provincetown
Provincetown is seated on the Northern tip of Cape Cod, with the Town of Truro as its only neighbor. Bordered by the Massachusetts Bay to the Northwest and North, Cape Cod Bay to the west and south, and the Atlantic Ocean to the Northeast, Provincetown is the perfect beach town.
This town is a favorite vacation spot for summer tourists because of its numerous beaches and unending trails. However, summer is not the only perfect time to visit this small town; winter also comes with endless possibilities and activities.
Winter is the perfect time to stroll around the beaches in Provincetown. The beach sides are usually very quiet, making enjoying the cold sea breeze and breathtaking views easy. The hiking trails are open all year round. Hike up the Beech trail for the perfect bird-watching experience. From hotels to Bed and Breakfast, this town has numerous accommodation options. You can stay at either Benchmark Inn or the Province Hotel.
Rockport
Rockport is a small seaside town at the tip of the Cape Ann Peninsula whose only neighboring town is Gloucester. Rockport is surrounded mostly by the Atlantic Ocean, offering visitors an array of pristine beaches and a stunning seaside view.
Winter season gives this town a different glow. Visit Motif #1, an 18th-century shack with a picture-perfect seaside view. Join hundreds of tourists to celebrate the art culture in Rockport. The art colony in this town is one of the oldest in America, with over 30 art galleries and hundreds of beautiful artworks.
There is a lot to see and do in this beautiful town. Explore this town from the comfort of any of the available accommodation options, like the Lantana House B&B or Addison Choate.
Sandwich
Sandwich is the oldest town on Cape Cod. It is beautifully seated at the entrance of Cape Cod Bay into the Cape Cod Canal. The motto of this town is "Post tot Naufracia Portus," meaning "after so many shipwrecks, a haven."
This town ranked 38 on Country Living Magazine's "Top 40 prettiest American towns to visit during the Winter." The Sandwich Boardwalk is a nice place to start your winter getaway. The boardwalk gives you a stunning view of the salt marshes around this area. You can access the beautiful Town Neck Beach from the boardwalk, which gives you a breathtaking view of the Cape Cod Landscape.
With multiple accommodations, you can stay at a Bed and Breakfast, like the Cape Cod Inn, or at a modern hotel, like the Sandwich Lodge and Resort.
Oak Bluffs
Oak Bluffs is a small town on Martha's Vineyard Island. The town is littered with Gingerbread cottages and well-preserved 19th-century buildings. The town is home to several beaches. The winter season gives a special glow-up to this small island town.
Wandering around the downtown area on foot and discovering its hidden gems are the highlights of your stay in Oak Bluffs. Visiting Inkwell Beach is famous for the African Americans who frequented the beach in the 19th century. Stroll along the beachside and see what sea treasures you can find. To get the best of your winter getaway, stay at any of the world-class accommodations in Oak Bluffs, like the Island Inn or the Morgan Hotel Martha's Vineyard.
Stockbridge
Stockbridge is a picture-perfect small town located along the Housatonic River in the Berkshire Hills. In the winter season, popular summer spots turn into beautiful winter gems. Thought of visiting Stockbridge in the Summer? Here is why you should visit in winter.
Stonebridge Bowl is a famous boating spot in Summer, but in Winter, this same spot becomes an ice-fishing location for families. Watch the beautiful flora collections at the Berkshire Gardens bloom. The Norman Rockwell Museum put up special events to celebrate the winter festivities. Learn about the rich history of this town from the knowledgeable Inn-Keepers at the different accommodation options in town, like Berkshire Days Inn and Devonfield Inn.
Williamstown
Williamstown is at the northwestern end of Massachusetts, sharing borders with Vermont and New York. Stepping into this town in winter is like stepping into the perfect winter wonderland. Skiing is a favorite winter sport for tourists and locals.
Williamstown is filled with several ski trails that are both groomed and ungroomed. Bob's Ski Loop is a perfect place to test your skiing skills. Art lovers will have a splendid time discovering the amazing art pieces at the Clark Arts Institute. Downtown Williamstown has beautiful scenery that is perfect for taking pictures. Check out the shops around this area.
You can stay at Fairfield Inn and Suites or the Clover Hill Farm to enjoy a nice and cozy time in Williamstown.
Lenox
Lenox is a small town in Berkshire County. This town is the summer home of the Boston Symphony Orchestra, which produces the Tanglewood Music Festival. The town's locals are welcoming, and they extend a hand of hospitality to tourists from different parts of the world.
There are a number of activities to do in and around Lenox during Winter. From Skiing to snowmobiling, Lenox is a perfect winter wonderland. You can visit the Hilltop Orchards and have a taste of their finest wines after skiing along its ski trails. Explore the array of winter events and activities in Lenox from any of the accommodation options like Brook Farm Inn.
Chatham
Chatham is at the Southeast tip of Cape Cod in Barnstable County. The town has been known over the years as a fishing community. This town is a beautiful place to visit all year round.
A major attraction in Chatham is the Chatham Light. The Chatham Light is an operating lighthouse operated by the United States Coast Guards. You can also watch the wildlife in its natural habitat at the Monomoy National Wildlife Refuge. Don't forget to watch the Seals in the water surrounding Chatham Lighthouse Beach. Get the best out of the town when you lodge at Chatham Bars Inn.
Marblehead
In Marblehead lies a peninsula that extends into the Massachusetts Bay. There is a nearby Island attached to the town called Marblehead Neck. The town is popular for its rich American history. It is also known as the birthplace of the American Navy.
Marblehead is a historic town filled with many historical buildings and sites. The perfect time to visit these places is in the winter when they have less crowd trooping in. This gives you enough time to explore and discover hidden secrets about the town. One such place is the Jeremiah Lee Mansion, built in the 17th century.
Lodging at any of the old-fashioned Inns in town, like the Harbor Light Inn, gives you the opportunity to share the wisdom of the Innkeepers.
Ipswich
Ipswich is a small coastal town in Essex County. This small town is home to locations for extraordinary activities, from Willowdale State Forest to Crane Beach. The town's terrains have activities that keep tourists trooping in all year round.
Appleton Farms is a major highlight in this town; tourists get to enjoy a fun family time performing well-curated activities on the farm. In winter, the farm area is perfect for cross-country skiing. Visiting the beach might not look like a good idea in winter, but taking a walk along the shorelines at Crane's Beach is very soothing. To complete your winter getaway fun, stay at the Ipswich Inn.
Foxborough
Foxborough is a small town in Norfolk County, about 22 miles away from Boston. The short distance between this town and Boston makes it a perfect winter getaway option. For people looking to have a quiet time away from the constant hustle and bustle of their lives, Foxborough is the right place to go.
Outside of the regular winter activities, Foxborough has a number of indoor activities perfect for the winter cold. You can explore the Memorial hall dedicated to people who have served in the armed forces. You can also catch a game or two at the Gillette Stadium. To enjoy your winter stay at Foxborough, you should stay at any of the accommodation options like America's Best Value Inn.
Massachusetts is a beautiful state in the New England region of the United States. Sharing boundaries with the Atlantic Ocean and the Gulf of Maine gives this state a beautiful view and loads it with activities all year round.
The fear of cold and frostbite should not stop you from exploring this perfect Bay state. To ensure you have a fantastic time in the state, here are the 12 best towns in Massachusetts for a winter getaway. With this, all you need to do is pack your bags and book the next flight down to the Bay State.
