What’s So Great About Great Barrington? A Weekend Guide to the Quietly Cool Berkshire Town

Unlike the Catskills Mountain region, which is far more sprawled out, punctuated only by quaint, post-industrial towns that are a little out of the way from the nature you drove up to see, Great Barrington lies at the foot of Monument Mountain and Mount Everett. Officially named an Appalachian Trail community in 2009, laying out a welcome mat and resources to the millions of hikers that pass through each year, the scenery is a constant reminder of all the possible activities to be enjoyed.

With over 7,200 acres of state forest and hundreds of easily accessible trails only moments from the town’s center, visitors truly get to choose their own adventure. Take a cinematic cruise down the long flat farm roads, cooing at highland cattle and relaxed quarter horses, or stop to collect a local farmer’s bounty in exchange for a few dollars in the honor system jar. Climb to one of the various summits overlooking the mountain range and the Housatonic River and pause to marvel at the natural ponds and more evergreens than you ever expected to find south of Vermont. Pick up the local Shoppers’ Guide and bounce from antique fair to tag sale to barn sale, collecting rare and valuable items that haven’t yet been priced with a tourist’s inflation. Walk around town while 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. Ski, snowboard, or snowshoe at Butternut or Catamount in the winter. Take a dip in the Green River in the summer. Enjoy cuisine that rivals some of New York’s best, and art galleries and live music that you can experience without ever having to move your car. Afterwards, if you can bear to part with the town, a drive back to New York is supremely scenic. Better yet, spend the night at a local inn, which is likely snuggled up to a babbling brook or farmstead. There you’ll understand what makes Great Barrington so great.

Here, your weekend guide to the Berkshire town:

Where to Stay

The Granville House

You won’t find a lot of hotels in Great Barrington, and that’s part of how it preserves its retreat-like quality. Of a small collection of inns right within the borders of town, the historic Granville House, built in 1825, is a charming and hospitable option. There are five rooms in the intimate inn, tastefully decorated with no luxuries spared. Around the inn you’ll find rare antiques and retro touches like a jukebox and pool table. Outside you’ll find sprawling views, peace and quiet, all only a three minute drive from downtown Great Barrington.