Road Tripping

The Appalachian Trail

If you’re looking for a road trip to get your blood pumping, immerse yourself in stunning natural habits and then jump on the Appalachian Trail running through Berkshire County.


Hop across the border into New York and discover the hamlet of Hudson. The Brooklyn effect is rippling upstate and giving some attitude to this nice-as-pie, riverside whistle stop.

North Adams

Right next door to Williamstown, North Adams is a former mill town that boasts an emerging art scene and MASS MoCA, the country’s largest center for contemporary visual and performing arts.


Less than an hour’s drive from The Briarcliff, up in North County’s burgeoning arts community, sits the college town of Williamstown. Home to prestigious Williams College and The Clark Museum.


Centrally located in heart of Berkshire County, Pittsfield's urban center is home to such cultural icons as the historic Colonial Theatre, the Berkshire Museum, and the Barrington Stage Company.


The town of Lenox is a popular destination known for its art galleries, shopping, upscale restaurants and Tanglewood, the legendary music venue and summer home to the Boston Symphony Orchestra.


Head a few miles north and discover the village of Stockbridge. Stroll Main Street and follow in the footsteps of Norman Rockwell, one of areas most famous residents.

Great Barrington

Just down the road, Great Barrington is a thriving place to live, work, and visit year-round. Smithsonian Magazine named it #1 on its 2012 list of 20 Best Small Towns in America.