Great Barrington, MA Travel Guide: The Most Charming Town in the Berkshires

Unlike the much larger Catskills Mountain region, punctuated only by quaint post-industrial towns that are a bit of a seclusion from the wilderness you visited by car, Great Barrington sits at the base of Monument Mountain and from Mount Everett. Officially named the Appalachian Trail Community in 2009, offering a welcome mat and resources to the millions of hikers who cross each year, the landscape is a constant reminder of all possible activities.

With over 7,200 acres of state forest and hundreds of easily accessible trails just minutes from downtown, visitors can truly choose their own adventure. Take a cinematic cruise along the long, flat farm roads, cooing past relaxed upland cattle and quarter horses, or stop to collect a local farmer’s bounty in exchange for a few dollars in the system’s pot. ‘honor. Climb to one of the various peaks overlooking the mountain range and the Housatonic River, and pause to marvel at natural ponds and more evergreens than you ever imagined finding in southern Vermont. Pick up the local buyers guide and go from antiques fair to tag sale to barn sale, collecting rare and valuable items that have yet to be valued with the inflation of a tourist. Stroll through town sipping coffee from Fuel and satisfy a sweet tooth with ice cream from SoCo Creamery or a bag of rare licorice from Robin’s Candy Shop. Skiing, snowboarding or snowshoeing in Butternut or Catamount in winter. Take a dip in the green river in summer. Enjoy cuisine that rivals some of New York’s best, art galleries, and live music that you can experience without ever having to move your car. Then, if you can bear to part with the city, a drive back to New York is extremely scenic. Better yet, spend the night at a local inn, which is likely snuggled up against a stream or a farm. There you will understand what makes Great Barrington so great.

Here, your weekend guide in Berkshire town:

Where to stay

The Granville House

You won’t find many hotels in Great Barrington, and that’s part of how it maintains its quality of retreat. Among a small collection of inns just inside the city limits, the historic Granville House, built in 1825, is a charming and hospitable option. There are five bedrooms in the intimate inn, tastefully decorated with no luxury spared. Around the inn you will find rare antiques and retro touches like a jukebox and pool table. Outside you’ll find stunning views, peace and quiet, all just a three minute drive from Great Barrington town center.

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