Activities
Go apple picking at this family-owned apple orchard in the heart of the Berkshires! It offers delicious apples, cider, and baked goods.
The Mount is a country house in Lenox which was the home of the noted American author Edith Wharton. She designed the house and its grounds. You can walk around the estate's gardens (with dogs!), eat at the Terrace Cafe, and pay a small admission ticket price to venture into the home itself.
Chesterwood was the summer estate and studio of American sculptor Daniel Chester French, whose most famous works include the Lincoln Memorial. Most of the 150-acre estate is now owned by the National Trust for Historic Preservation, which operates the property as a museum and sculpture garden.
Naumkeag is a public garden and the former country estate of noted New York City lawyer Joseph Hodges Choate and Caroline Dutcher Sterling Choate. Each October, they host the "Incredible Naumkeag Pumpkin Show!"
This hike is one of the most popular in The Berkshires. From the 1,642ft summit, you’ll enjoy views as far north as Mount Greylock, near the Vermont border, and, in the western distance, the Catskills of New York. The trails offer several "loop” options, none longer than three miles (1.51-mile Indian Monument Trail, 0.83-mile Hickey Trail, and 0.62-mile Squaw Peak Trail).
Cobble Hill Loop is a 2.1 mile, moderate loop trail located near Tyringham, MA. It features beautiful wild flowers and dogs are also able to use this trail!
Hancock Shaker Village is a living history museum whose mission is to bring the Shaker story to life. In addition to viewing the architecture, you can see the farm and gardens, the animals, costumed interpreters, demonstrations of handicrafts like weaving, spinning, and blacksmithing, hiking and walking trails, and photo and art exhibitions.
The Norman Rockwell Museum is an art museum in Stockbridge dedicated to the art of Norman Rockwell. It is home to the world's largest collection of original Rockwell art.
Go sip on some wine while sitting in Adirondack chairs overlooking the beautiful Berkshire landscapes. Sometimes there are food trucks and live music as well!
Mooncloud is a cocktail bar in downtown Great Barrington. We recommend grabbing a cocktail-to-go from Mooncloud and then wandering around the adorable storefronts of downtown Great Barrington.
Mark Firth started Diner and Marlow & Sons in Brooklyn before packing up and opening this farm-to-table restaurant in the Berkshires. The place is fun and lively. Go early and have a drink at the bar, it’s a great scene.
Six Depot is Melanie and Cody's favorite spot for quick bites and delicious baked goods! It is a small-batch coffee roastery and cafe located in the oldest train station in the Berkshires.