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The Berkshires

Escape into the Mountains of Western Massachusetts


There are few trips within a couple hours’ travel of Fairfield County that can match the intrinsic joy of a weekend getaway in the Berkshires of Massachusetts. Whether you’re looking for an active few days of paddling, hiking and biking or wanting to cozy up in a bed and breakfast to read a good book, drink some local wine and breathe in the fresh air and quiet of a small historic mountain town, you can find it all within the timeless valleys and peaks of western Massachusetts.  

A great trip to the Berkshires is not complete without a slow scenic drive on Connecticut’s sleepy Route 7. Don’t be in too much of a hurry to get to your hotel or campsite, as the way there is in ways just as enjoyable as your stay. Make sure to have ample time scheduled for en route winery tours, stops at antique shops, scenic views or anything else that calls to you. From the moment you get in your car to the fleeting moments of the end of your journey, a trip to the Berkshires will not disappoint.

Towns to Check Out

Great Barrington

Stay and Eat

The Old Inn on the Green- New Marlborough
Blantyre Inn- Lenox
Red Lion Inn- Lenox
Cranwell Inn-Lenox
Stockbridge Inn-Stockbridge

Shop and Walk

Great Barrington
Explore the beautiful downtown area for a unique mix of historic charm and New York chic. Shopping options include a great used bookstore, art galleries, eclectic jewelry and home furnishings, outdoor gear and apparel and great food (Be sure to check out Rubiner’s Cheese Mongers for a treat of artisan cheeses and smoked meats)


Monument Mountain-Great Barrington
Ice Glen-Stockbridge
Appalachian Trail-Multiple Spots


Scenic Biking

Go See

Mahaiwe Performing Arts Theatre-Great Barrington

Berkshire Tourism

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