Things To Do - Places To Visit

The Berkshire Hills are rich in history and culture, not just skiing. Some quaint New England towns surround Ski Butternut, each offering a diverse and unique flavor. Read the quick descriptions below then visit these historic towns for a first hand account. Find out why Smithsonian Magazine named Great Barrington the Best Small Town in America.


Great Barrington

Ranked as the #1 Small Town in America by Smithsonian, and heralded as "a ski destination town" by SKI Magazine, Great Barrington has something for everyone! Within the town limits there are over 65 restaurants, numerous B&B's, amazing country inns, hotels and motels, as well as four movie theaters, a bowling alley with indoor miniature golf and museums. This is the quintessential classic New England ski town. Its vibrant downtown district includes Railroad Street, one of the oldest streets in the country, and Main Street, the first street in the country to have electric lights. This district was also the site of many historic events including the first armed resistance with the British over taxes. And the historic Shay's Rebellion which tested the new Union of states. Great Barrington is also the place where the first slave was set free. A new addition to the community is the Southern Berkshire Community Center where you can enjoy a swim and revive the legs in a warm sauna after your day on the mountain! For more detailed information, The Southern Berkshire Chamber of Commerce can be reached at



The oldest town in the Berkshires, Sheffield, was purchased from Chief Konkopot and other Stockbridge Indians in 1724. Its first settler was Matthew Noble of Westfield who arrived in 1725. He described his new hometown as a “hideous howling wilderness.” Incorporated in 1733, Sheffield has remained rich in agriculture production. A scenic setting of mountains and river valley, Sheffield has become a visitor destination sought for its beauty and its many offerings of antique stores, B&B's and world-class restaurants.


Stockbridge is a town that truly represents the New England spirit. It's famous for the Norman Rockwell Museum, the elegant Red Lion Inn and the studio of Daniel Chester French. Its unique downtown is home to many shops, galleries, restaurants, as well as many historic homes, which date back to the 1700's. Something to look for: each December, Stockbridge recreates the Norman Rockwell Main Street Winter for families of all ages!



The summer home of the Boston Symphony Orchestra at Tanglewood is nestled in a corner of the Berkshires in Lenox. The town offers a diverse range of restaurants, arts and crafts stores and galleries. It was renowned as a gathering place for the nations early millionaires. Many of the original "Berkshire Cottages" of Lenox have been converted into elegant inns, bed and breakfast establishments, the famed Canyon Ranch Spa, Shakespeare & Co., Blantyre, Wheatleigh and the Kripalu yoga institute. The town also features a number of parks and a wildlife sanctuary.



The historic town of Lee is situated along the banks of the Housatonic River. The town is on the list of the National Register of Historic Places. Cranwell Resort, Spa and Golf is one of the converted Berkshire mansions. Lee offers a fine assortment of restaurants, shops, many service businesses and the 64-store Lee Premium Outlets. The beautiful downtown Main Street is lined with wrought iron lamps, flowerbeds and freshly painted stores.

Contact the Berkshire Visitors Bureau at (800) 237-5747 or to learn more about our beautiful Berkshires and why so many skiers and other winter guests come to the area to enjoy their family vacation.