Things To Do
Monument Mountain
For the best scenic overlook near Great Barrington, head to Monument Mountain. Located just off Route 7, the Peeskawso Peak Trail offers breathtaking, sweeping views of the Berkshires and the Housatonic River Valley from high atop dramatic cliff faces.
Olivia's Overlook at Yokun Ridge Reserve
At the center of the Yukon Ridge S reserve is a must visit place for the best views of the lake Mahkeenac or Stockbridge bowl. The land and all of the present-day Berkshires are the ancestral home of the Mohican people who were forcibly displaced to Wisconsin. These lands continue to be of great significance to the Stockbridge Munsee Mohican Nation today.
Kennedy Park
Kennedy Park in Lenox is a hardwood forest with old carriage roads and nearly 15 miles of groomed trails.
Tanglewood
Tanglewood is an iconic outdoor music venue nestled in the Berkshires of western Massachusetts and the summer home of the Boston Symphony Orchestra. Known for its beautiful scenery, open lawns, and world-class performances, it has become one of the region’s most beloved cultural destinations.
Norman Rockwell Museum
Norman Rockwell Museum is home to the world’s largest collection of original works by Norman Rockwell. Located in the scenic Berkshires, the museum celebrates Rockwell’s iconic illustrations and storytelling while offering beautiful grounds, galleries, and exhibits that highlight American art and culture.
Shopping in Great Barrington
Shopping in Great Barrington is a highly walkable, boutique-heavy experience. Centered around Main Street and Railroad Street, the downtown area is packed with artisanal shops, independent bookstores, high-end galleries, and specialty food purveyors—with almost no chain stores.
Shopping in Lenox
Shopping in Lenox, MA, is a highly walkable, boutique-heavy experience. Centered around Church and Main Streets, the downtown area features a charming collection of upscale clothing boutiques, art galleries, high-end home décor, and specialty gift shops, with no large chain stores.
Stockbridge, MA
Stockbridge, MA, is most famous for its quintessential New England charm, classic art, and rich cultural history. The town is best known as the longtime home of painter Norman Rockwell and is immortalized in his iconic painting Stockbridge Main Street at Christmas.
Bartlett's Orchard
Bartlett's Orchard & Farm Market is a family-owned apple orchard and year-round country store located on Lenox Mountain in the Berkshires. Although commonly associated with neighboring Lenox, it is actually situated in Richmond, MA (About 15 minutes from Lenox).
Barrington Brewery & Restaurant
Barrington Brewery & Restaurant is a pioneering brewpub in Great Barrington, Massachusetts, known for producing its "Barn Brewed" beer using massive solar panel systems to heat water and generate electricity. Established in 1995, it is one of the world's most prominent solar-powered breweries.
Antimony Brewing - Craft Brewery & Kitchen
Antimony Brewing is a popular brewpub located in Lenox, Massachusetts. Known for its on-site 7-barrel brewhouse and scratch-kitchen, the venue features award-winning craft beers alongside pub-style food, burgers, and brick-oven pizza.
Kripalu Center For Yoga & Health
Kripalu is the largest yoga and holistic health retreat center in North America, located in Stockbridge, Massachusetts. It offers immersive wellness programs, daily yoga classes, Ayurveda training, and "R&R" (Rest and Renewal) getaways on a sprawling, nature-focused campus.