When you think of Massachusetts, there's a good chance the first city, town, or region you would think of is Boston, Cape Cod, Salem, Cambridge, or Nantucket/Martha's Vineyard. There are definitely lots of other great spots throughout the state that I'm leaving out. But what about some of those other places around the Bay State that don't necessarily get the notoriety. Those are the more underrated places around the state. It just so happens that the Berkshires is home to not one, but four of those spots.

World Atlas has released their list of the most underrated towns in Massachusetts. There are some spots that you might not be surprised to see. These are places that residents here may know if, but if you're a tourist, you might just overlook one of these hidden gems.

So, what are these four underrated towns in the Berkshires?

1. Great Barrington, MA

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The picturesque town has not just the historic downtown setting, but the outdoor surroundings make it a pick, according to World Atlas:

The lively and attractive town of Great Barrington is located in the majestic Berkshire Mountains and is a haven for both culture enthusiasts and nature lovers. This charming town is home to numerous alluring and fascinating cultural attractions that are sure to pique the interest of any wanderlust tourist. The quaint shops, fine dining establishments, and compelling art galleries in the historic downtown district make it the ideal place for an afternoon stroll. Nearby Monument Mountain offers stunning views of the expansive countryside for anyone looking to fully immerse themselves in the area's natural splendor. For those looking for outdoor activities like fishing, kayaking, and picnics, the Great Barrington Riverwalk, a lovely trail that meanders alongside the Housatonic River, is the perfect location.

2. Adams

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Mount Greylock highlights the reasons why Adams makes the list of the most underrated towns in Massachusetts.

It is said that variety is the spice of life, and that's exactly what one can expect when exploring Adams. From the majestic heights of Mount Greylock to the tranquil beauty of the Cheshire Reservoir, the town offers a diverse range of experiences that are sure to leave visitors thoroughly enchanted. Whether it's a peaceful walk along the Ashuwillticook Rail Trail or an adventurous trek up the steep slopes of Mount Greylock, there's something for everyone in this idyllic town.

 

3. North Adams

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World Atlas emphasizes the historic nature of North Adams' downtown on their list:

The vibrant and energetic community of North Adams is home to a diverse tapestry of history and culture. It is a place where travelers are encouraged to partake in a range of pursuits and submerge themselves in a realm of artistic delight...It also promises to enthrall the senses to explore the historic downtown district with its varied mix of shops, restaurants, and art galleries.

 

4. Sheffield, MA

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The Berkshire County town turned 290 years old in 2023 as it was founded back in 1733. Here's what World Atlas had to say about it:

Sheffield is like a time capsule that perfectly captures the spirit of the past. Its charming streets have an antiquated charm that transports people to bygone eras. The charming alleyways can be explored while taking in the fabled location's rich history...The Housatonic River also provides a sublime escape from the stresses of contemporary life with its swaying currents and ethereal views. For those looking for a break from the hustle and bustle of city life, Sheffield is an absolute must-see destination due to the wide variety of activities available there, from antiquing to hiking.

Honorable Mention: Charlemont

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This town that is NOT technically part of the Berkshires also made the list. However, as a border town, it is home to a popular ski resort that received some love from World Atlas in their list.

Adventurers can partake in heart-pounding white water rafting trips on the pure Deerfield River, go on breathtaking walks along the illustrious Mohawk Trail, or explore the magnificent Hawley Bog Preserve, a serene sanctuary home to a variety of unique flora and animals. The famed Berkshire East Mountain Resort, a top spot for fans of skiing, snowboarding, and other winter sports, opens its slopes to visitors during the colder months.

Of course, to those that reside within the Berkshires, it should be no surprise that we had more than a couple spots show up on a list that mentions the most underrated towns in Massachusetts. But that's also just what makes them so great!

8 Massachusetts Cities That Have the Best Downtowns

10 Things That May Shock You About Moving to The Berkshires

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