Skip to content

Things to do in Berkshire County

Top recommendations from locals

From sightseeing to hidden gems, find out what makes the city unique with the help of the locals who know it best.
Concert Hall
“Great Place to see Live music outside, Bring a Picnic, Wine and Blanket relax and listen to the music”
  • 162 locals recommend
Art Museum
“A sensory experience! I love MASS MoCA's ever-changing array of contemporary art, and the architecture of the old mill buildings even more. ”
  • 107 locals recommend
Art Museum
“The Clark Art while it’s closed due to COVID 19, has excellent hiking trails. ”
  • 94 locals recommend
Café
$
“Beautiful area Great for a lovely day in Berkshires, Dance feastible all summer long, every Dance venue.”
  • 93 locals recommend
Nature
“Hillsdale, NY: 35 minute drive from house. Modest ski resort with 7 lifts, 3 terrain parks, 36 trails, night riding & equipment rentals.”
  • 85 locals recommend
Art Museum
“Great place to walk the grounds see the covers of magazine that made history, see where it happened and learn his story”
  • 103 locals recommend
Trail
“Amazing in all four seasons. Enter on the NY border for a more relaxed 15 minute hike to the falls. Or enter on the Massachusetts side for a 5 min, slightly more challenging hike. Picnic, swim, hike, great spot for photos!”
  • 81 locals recommend
American Restaurant
$$
“Prairie Whale – 30 mins - One of our favorites. If you’re familiar with Andrew Tarlow (Diner, Marlow and Sons, etc…) then you’ll get the vibe of Prairie Whale. ”
  • 63 locals recommend
Natural Feature
“On a hot summer day, a drive up to the summit of Mt. Greylock can be a nice way to cool down. The views from the top are spectacular and Bascom Lodge at the top is nice lunch stop.”
  • 55 locals recommend
Place to shop
“Ski Butternut is a great family atmosphere ski area. It’s not the biggest mountain but it has something for everyone, with lots of Berkshire charm. ”
  • 54 locals recommend
Grocery or Supermarket
“This place is a top-notch grocery store that you can get all your specialty food items at. Great for sandwiches or to grab some food for a picnic at Tanglewood or even at home to cook!”
  • 67 locals recommend
Shopping Centre
“A very comfortable drive north into Massachusetts, taking exactly one hour. Hill top, open store shopping for the whole family.”
  • 30 locals recommend
Scenic Viewpoint
“Easy trails, the summit has great views. Park and walk, very convenient. If you like to run you can even run to the mountain and then hike! only 4 miles from the home.”
  • 38 locals recommend
Pizza Place
$$
“For wood-fired pies with sourdough crust and gourmet toppings, as well as large salads and a lively atmosphere, check out Baba Louie's. This is a local favorite, so there may be a wait at peak times.”
  • 43 locals recommend
Performing Arts Venue
“Great shows--recents have included John Mulaney, Natalie Merchant, Paul Taylor Dance Company. They also show movies, HD opera and other performance events. Check it out!”
  • 34 locals recommend
University
“Just a short drive to this theater in Lenox, Ma. Check theater on line for performances and schedule.”
  • 43 locals recommend

Top restaurants

American Restaurant
“Prairie Whale – 30 mins - One of our favorites. If you’re familiar with Andrew Tarlow (Diner, Marlow and Sons, etc…) then you’ll get the vibe of Prairie Whale. ”
  • 63 locals recommend
Pizza Place
“For wood-fired pies with sourdough crust and gourmet toppings, as well as large salads and a lively atmosphere, check out Baba Louie's. This is a local favorite, so there may be a wait at peak times.”
  • 43 locals recommend
Bar
“Charming local bar and eatery. Short walk from MassMOCA in downtown North Adams.”
  • 29 locals recommend
American Restaurant
“Outstanding drinks and great american fare. This is a great farm to table restaurant and reservations are almost a must unless you sit at the bar. There’s a cozy nook where you don’t need reservations but there’s often a wait. ”
  • 34 locals recommend
Bar
“Bizen has the largest menu of Japanese food I’ve ever seen. Enjoy this delicious treat!”
  • 35 locals recommend
Restaurant
“Great bar, consistent performance on menu and ideal location in Great Barrington, Allium delivers the goods when you find yourself downtown.”
  • 24 locals recommend
Bar
“Best high-end food in the region. Friendly bar perfect for solo diners looking for a great meal. ”
  • 25 locals recommend
Restaurant
“Wonderful food and ambiance. Worthwhile dining experience. Cozy and the dessert menu is noteworthy.”
  • 29 locals recommend

Get to know Berkshire County

Explore more on Airbnb