Check out the cute shops, grab a coffee from Fuel, lunch from Rubi's Cafe, or dinner from Prairie Whale. End the night at Soco Creamery or grab a cocktail from Moon Cloud.
Take in views of the Housatonic River Valley from the top of the summit or check out other spots to hike in the area like the Housatonic Flats Reserve.
Lenox is a nearby town with several art galleries, shops, and restaurants. Try Patisserie Lenox for lunch and specialty French pastries or book a table at Bistro Zinc for dinner. You can also do some additional hiking and enjoy the scenery at the Pleasant Valley Wildlife Sanctuary.
Check out the Norman Rockwell Museum, the Chesterwood Historic Home, Naumkeag House & Gardens, or the Berkshire Botanical Garden. Stop at The Lost Lamb or Peace, Love & Chocolate for coffee and a sweet treat, or grab dinner from Once Upon a Table.
Ten minutes south of Great Barrington you can find the Berkshire Mountain Distillers (home of the award-winning Greylock Gin, Ice Glen Vodka, and Berkshire Bourbon). If you're craving a pint instead, Big Elm Brewery & Taproom is just down the street. Check out Bartholomew's Cobble Reservation or Race Brook Falls for hiking trails and views, or stop at Roberto's Pizza for lunch.