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Things to do in Pittsfield

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.
Bar
$$
“Many refer to this place as "the best beer joint in the Berkshires." They also serve food. ”
  • 5 locals recommend
Natural Feature
“Great FREE Swimming at south end of lake. Park on Hancock Rd off route 7 North Lanesboro, just north of Zucchini's Restaurant. There are boat and jet ski rentals further north on Rt 7 on the lakeside.”
  • 5 locals recommend
Park
“Nice looped trails, mostly flat and wooded, some through wetland areas. Beautiful large pines and a nice meadow view at the start of the hike. It's very close and makes a good quick walk.”
  • 6 locals recommend
Restaurant
“Informal dining, Breakfast lunch dinner, family friendly. healthy food, even vegan and GF options. Operated by Richard Bourdon, the sourdough bread bakery in Housatonic and AURA, the former owner chef of the beloved CAFE RIVA on Tyler Street, which closed at the height of popularity due to landlord/building difficulties some years back. She also ran food concession at Berkshire Organics "NatAURAly" for several years in the interim.”
  • 4 locals recommend
Natural Feature
“A nice lake for swimming and boating, large field for picnics or frisbee, and a concert pavilion. A google search for "Onota Lake Beach" will get you to the public beach, "Live on the Lake" will yield the concerts going on in the pavilion.”
  • 7 locals recommend
Lodging
“Occasional great live music and Djs, this hotel/restaurant/bar is the perfect place to visit if you would like to get dressed up and have a beautiful dinner with a great, unique atmosphere. Recently renovated and in a great part of the city.”
  • 3 locals recommend
Cafe
“Located in the center of Pittsfield. Recommended by my other guest. You can just coffee or a meal.”
  • 4 locals recommend
Restaurant
$$
“Best Italian restaurant in the North East. Make reservations. They get busy.”
  • 7 locals recommend
Liquor Store
“Extensive selection of wines, beer, and liquor. Also offers artisinal cheeses, specialty foods, discount liquors, craft beers and much more… A great place for specialty food gifts.”
  • 5 locals recommend
Pharmacy
“Groceries nearby - we should have included a discount card there, or just ask for the store card!”
  • 4 locals recommend
Cafe
$$
“Family owned with a charming atmosphere. Delicious Italian food and fantastic family style salads everytime. Make a reservation. Sit downstairs to watch the chef or upstairs for quiet ambiance. ”
  • 5 locals recommend
Breakfast Spot
$
“Informal restaurant, breakfast, lunch dinner, something for everyone, family friendly.”
  • 3 locals recommend
Indie Theater
“Great performances of both contemporary and well established theater and dance. In Pittsfield, MA, about 20 minutes away.”
  • 5 locals recommend
Grocery or Supermarket
“Apple picking and fresh cider doughnuts! Worth a stop if you are looking for some local foods or edible gifts to take home with you, and especially if you are heading to West Stockbridge - despite it's unappealing name, Swamp Road is stunning!”
  • 9 locals recommend
Park
“An 11 mile path that is mostly flat and paved. Great for a stroll, a bike ride, running or rollerblading! Take a left out of the driveway and head north on Old State Rd about 3/4 of a mile, where the rail trail crosses the road. A right will take you to the start of the trail, about two miles, and a left will take you about 9 miles North if you follow it all the way! Beautiful mountain and water views. You'll' go by the spot where the photo on the front of this book was taken ;)”
  • 8 locals recommend
Store
“In Pittsfield, a nice store for an ecletic mix of big posters, cards, bags, scarves, garden ware, that kind of thing. They are picture framers too. Right next to the Berkshire Museum.”
  • 2 locals recommend