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Where to Get Off the Beaten Path in the Berkshires

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The mountainous area of Western Massachusetts known as the Berkshires is one of those magical places that’s gorgeous any time of year, and is chock-full of nature excursions, cultural activities, and superb food and drink. While places like Tanglewood and MASS MoCA tend to get all the glory (and for good reason—they’re awesome), there are also countless under-the-radar spots that are worth exploring. Here are eight of them.
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Originally a railway line built in the mid-nineteenth century, the Ashuwillticook Rail Trail came about when train service stopped in the 1990s and local residents petitioned to turn the space into a recreational trail. Traversing 11.2 miles from...
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55 Pittsfield Rd, Lenox, MA 01240, USA
For a sweet reprieve, a stop at Chocolate Springs is a must. Owner and chocolatier Joshua Needleman is Culinary Institute of America–trained and put in his time at places like La Maison du Chocolat in Manhattan and Paris before opening up his own...
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125 W Bay Rd, Amherst, MA 01002, USA
If you’re one of the countless people who grew up reading Eric Carle books (or reading them to your children), then this gem of a museum is not to be missed. Started by the author and his late wife, the museum celebrates picture books from around...
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North Adam Road, Adams, MA 01220, USA
At 3,491 feet, Mount Greylock is the highest point in Massachusetts and became the state’s first wilderness state park in 1898. The 12,500-acre reserve, which is a favorite for multi-season hiking and recreation, is no secret, but what many don’t...
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Sure, you can go skiing at a major ski resort in the area. But for a little more wilderness and natural beauty, don’t miss local favorite Notchview, a 3,000-acre reservation that is gorgeous any time of year but a particular favorite in the...
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37 Church St, Lenox, MA 01240, USA
Chef Bjorn Somlo has been nominated for James Beard Awards multiple times so he’s not exactly under the radar, but many are still surprised to find a restaurant of this caliber in the Berkshires. The small, modern restaurant is situated directly...
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2 Main St, West Stockbridge, MA 01266, USA
When National Geographic photographer John Stanmeyer opened the Shaker Dam Coffeehouse & Stanmeyer Gallery in a nineteenth-century house in West Stockbridge in 2013, it instantly became a local favorite. The social justice–driven cafe serves...
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11 Gifford St, Pittsfield, MA 01201, USA
Wandering Star Brewery is pretty much the definition of "off the beaten path." Located in a garage in Pittsfield, this 10-beer craft brewery was started by three friends who met through the New York City craft brew scene. They opened up shop in...