3 Must-See Towns in the Berkshires

By Rachael Funk


A gem of New England, the Berkshires have been a refuge for artists, city dwellers looking for a retreat, and anyone longing for some peace and quiet. The Berkshires cover a large portion of western Massachusetts and are packed with charming towns to visit, so it may be overwhelming to pick which ones to see. If you’re a first-timer, here are a few of our favorite towns you can visit on your trip.


Lenox

For a classic Berkshires experience, spend a day in Lenox. Tucked into a lush area of the Southern Berkshires, this is the place to find your new home-away-from-home.
The area is rich with natural beauty and fascinating history. Here, you can find historic sights like Edith Wharton's former stately home, The Mount, where you can visit the mansion and stroll the extravagant gardens. In the summer, Lenox comes to life with productions from the Shakespeare & Company theatre and concerts during the Tanglewood Music Festival.


Stockbridge

Perhaps best known as the home of Norman Rockwell, Stockbridge is a cozy town with plenty to do.
The historic village offers boutique stores, art galleries, specialty food shops, and easy access to nature preserves and walking paths from the downtown area. Visit the Norman Rockwell Museum, spend an afternoon in the 15-acre Berkshire Botanical Garden, or tour the Historic Naumkeag Mansion And Gardens.
After you’ve explored the town, take your pick of nature trails. The Mary V. Flynn Trail is an easy, scenic walk through the woods along the Housatonic River. You’ll cross quaint wooden bridges, walk a gravel trail, and follow the old Berkshire Street Railway. For a more challenging hike, climb Laura’s Tower Trail. From the summit on a clear day, you can see New York’s Catskill Mountains and Vermont’s Green Mountains.


Great Barrington

Great Barrington is one of the largest cities in the Berkshires. Only about a 3-hour drive from Manhattan, this city is a happy medium between small-town life and big-city amenities.
The area has outstanding arts and cultural offerings through Barrington Stage Company and Mahaiwe Performing Arts Center as well as a bustling midtown and close proximity to outdoor adventure. From Great Barrington, you can easily reach the Housatonic River for some fly fishing, a scenic section of the Appalachian Trail, and Monument Mountain Reservation, where you can get spectacular views of the Housatonic River Valley from the summit.

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