12 Places Where You Can Still Experience Old Massachusetts
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Sophia
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While many people only see the touristy bits of Massachusetts when they visit, there’s an entire side of Massachusetts that most visitors never see. Old Massachusetts is full of simple but enchanting spots that represent our state’s history and the places where generations of Bay Staters have made memories. Here are a few spots that still have that old Massachusetts feel.
This quiet fishing village looks much as it did 100 years ago. It has some of the best harbor views on the North Shore and you’ll love wandering its quaint streets and ducking into its many cozy pubs.
This diner opened in the 1950s and has been a Northampton mainstay ever since. Though it's definitely family spot with comfort food like you dream about, the Bluebonnet also serves some pretty tasty cocktails and all-day breakfast. (324 King Street, Northampton)
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The Mohawk Trail was once a trade route for Native people in Massachusetts. Today, it's an incredibly scenic drive and special cultural region. It extends 69 miles from Athol to Williamstown and will take you through plenty of beautiful Berkshire mountain scenery.
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If you want to take "old" Massachusetts to the extreme, stop by Plimoth Plantation in Plymouth. This collection of outdoor "living history" exhibits includes a full-scale Pilgrim village, complete with wandering chickens, historians who speak to you as if they were really living in the 1600s, and fully-furnished homes with roaring fires and period furniture that you can explore at your leisure. There’s also a Wampanoag homesite where you can learn about how the Wampanoag peoples of Massachusetts once lived, as well as how they live today. (137 Warren Avenue, Plymouth)
This is another amazing living history museum where you can experience life as it was hundreds of years ago in Massachusetts. The village recreates life in rural New England during the late 1700s and early 1800s. You’ll get to visit with farm animals, learn old-fashioned handcrafts and enjoy pastoral surroundings. (1 Old Sturbridge Village Road, Sturbridge)
This Franklin County town is nestled against the Deerfield River and the Mohawk Trail. It offers a classic New England feel with plenty of natural beauty, plus lots of local shops and restaurants.
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This classic drive-in movie theater has been around for 62 years and counting. Featuring two screens and plenty of "seating," this spot is perfect for catching a film with a cupholder full of snacks. (35 Milford Street, Mendon)
This Martha’s Vineyard town is home to plenty of clapboard homes, fudge shops and nautical vibes. Don't miss a trip to Edgartown Harbor Light for amazing views.
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This place isn't anything fancy, but it has a perfect retro vibe and homestyle cooking that's just so comforting. You can also play classic hits at the jukeboxes on every table. (372 State Road, Whately)
The Cape Cod Provincelands Trail is a gorgeous waterfront path that will take you through some of the most unspoiled scenery in Massachusetts. The trail is about about 5.25 miles long and perfect for kids and groups.
Located between the Weir River and Hingham Harbor, World's End is a 251-acre conservation space with beauty to spare. You can walk old carriage paths and explore grassy meadows, beaches and shady forest.
The Smithsonian has ranked Great Barrington as the best small town in America, and it’s easy to agree. With its great location near the Taconic Mountains and a charming vibe centered around an old-fashioned Main Street, this town of 10,000ish people feels like a step back in time.
What do you consider old Massachusetts? Do you have any favorite classic spots? Let us know in the comments! For authentic Massachusetts intel, check out our list of some of the best mom and pop restaurants in the state here.
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