Things To Do
The Red Lion Inn
We love the smashburger at the Tavern, music in the Lion's Den, and playing cards/having cocktails on the porch. (Also the pool and hot tub are open year round and they don't really check to make sure you're staying there.)
The Dream Away Lodge
Farmhouse dining, eclectic menu. Joan Baez and Bob Dylan made music here, and there is live music many nights. Fire pits outside. A whole vibe.
Norman Rockwell Museum
Museum devoted to the life and work of Norman Rockwell, who lived and worked in the Berkshires. There is a charge for admission to the museum, but the grounds are beautiful and free to explore.
The Mount, Edith Wharton's Home
The sprawling historic home and grounds of Edith Wharton. Museum, architectural site, and landscaped paradise.
Berkshire Botanical Garden
Beautifully maintained gardens with a modest admission fee and a cafe on site.
Naumkeag
Experience Gilded Age style and splendor at this marvelous estate renowned for its elegant gardens and rare Berkshire “cottage.”
Tanglewood
2024 season has concluded, but you can explore the beautiful grounds of the famed Boston Symphony Orchestra's summer home (and the site of much of the film Maestro.)
GB Eats
Great breakfast/lunch spot in Downtown Great Barrington (the Bloody Mary's are stellar!)
Haven Cafe & Bakery
Yummy breakfast/lunch in Lenox. Get there early to avoid the inevitable line. It's worth it!
The Bistro Box
Roadside stand for burgers, shakes, and killer parmesan truffle fries. (Always a line. Get the bacon jam on your burger.)
Pizzeria Boema
Delicious pizza and a great cocktail/wine list. Gluten free crust option!
Baba Louie's Sourdough Pizza
Delicious sourdough crust pizza in the heart of downtown GB.
The Marketplace Kitchen and Cafe
Casual breakfast/lunch/coffee. Multiple locations throughout the county.
Xicohtencatl Restaurant
Mexican in GB. Lively, good portions. Great guac.
The Prairie Whale
Classy yet laid back farm to table dining. Seasonal menu, highly locally sourced.
Main Street Cafe
Old school storefront diner on Stockbridge's historic Main St.
Frankie's
Gorgeous Italian in a warm setting. Impressive wine list.
Monument Mountain
Well marked hiking trails, parking lot directly off Rte 7.
Kennedy Park
Town-owned & maintained hardwood forest with old carriage roads & nearly 15 miles of groomed trails, with a lookout point of a mountain vista.
New Marlboro Preserve
Mostly flat trails alongside babbling streams. Picks up directly across from Gedney Farm.
Ice Glen Trail
2 relatively short hike options - moss covered rocky terrain or hike to the observation tower. Both directly behind the Red Lion Inn.
Housatonic Flats Reserve
Easy, mostly flat loop trail along the Housatonic River in Great Barrington.
Calyx Berkshire Dispensary
Women owned, well curated flower shop in downtown GB.