All-season adventures
This is home base, and a destination by itself. Details: https://www.jiminypeak.com/
77 locals recommend
Jiminy Peak
This is home base, and a destination by itself. Details: https://www.jiminypeak.com/
Hike to the summit for views of the Housatonic River Valley. https://thetrustees.org/place/monument-mountain/
53 locals recommend
Monument Mountain
Hike to the summit for views of the Housatonic River Valley. https://thetrustees.org/place/monument-mountain/
Neighborhoods
Great place to shop and eat. See https://lenox.org/visit/. Famous for classical music at Tanglewood. https://www.bso.org/tanglewood
85 locals recommend
Lenox
Great place to shop and eat. See https://lenox.org/visit/. Famous for classical music at Tanglewood. https://www.bso.org/tanglewood
This nearby town offers mini golf, ice cream (the ever-popular Krispy Cones), antique shopping and indoor/outdoor dining at the Old Forge Restaurant.
6 locals recommend
Lanesborough
This nearby town offers mini golf, ice cream (the ever-popular Krispy Cones), antique shopping and indoor/outdoor dining at the Old Forge Restaurant.
Sightseeing
Open most of the year, this is one of the top attractions in the Berkshires.
161 locals recommend
Hancock Shaker Village
1843 W Housatonic StOpen most of the year, this is one of the top attractions in the Berkshires.
A world-class museum open year-round. https://www.clarkart.edu/visit/hours-and-admission
329 locals recommend
The Clark Art Institute
225 South StA world-class museum open year-round. https://www.clarkart.edu/visit/hours-and-admission
Performing arts
Award-winning theater. https://barringtonstageco.org/visit/
64 locals recommend
Barrington Stage Company
30 Union StAward-winning theater. https://barringtonstageco.org/visit/
One of the premier dance venues in the country. https://www.jacobspillow.org/
257 locals recommend
Jacob's Pillow
358 George Carter RdOne of the premier dance venues in the country. https://www.jacobspillow.org/
Food scene
The best apple cider donuts I've ever had. And there's wine, too!
41 locals recommend
Hilltop Orchards Home of Furnace Brook Winery
508 Canaan RdThe best apple cider donuts I've ever had. And there's wine, too!
Christiansen's Tavern
37 Corey RdOMG, the Mile High Fries are amazing (and huge). Right at the resort.