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Best things to do in Pittsfield

Discover the city according to locals. Find the best things to do, places to eat, and get priceless advice from the people who live here.

Café
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“The best place for the best selection of local , organic , vegetables, meat , fish and all kinds of mouthwatering treats.”
39 locals recommend
Museum
“Local color, including Nathaniel Hawthorne's writing desk where he wrote "The House of Seven Gables". Nice add on to a trip going downtown. About 8 minutes or less from the house.”
25 locals recommend
Point of Interest
“This ski area is only about 17 minutes away, in Pittsfield, MA. Not fancy but easy to reach and easy to use; discounted Thursday nights. ”
31 locals recommend
Theatre
“Restored to original beauty this theater has live performances weekly. Plays, live music, children's shows and many holiday performances. ”
14 locals recommend
Theatre
“Really the best of the Berkshire theatre scene. Always great productions. 29 miles.”
17 locals recommend
Indie Cinema
“A great alternative to the mall; the Beacon in Pittsfield always runs great movies with good popcorn and very comfortable stadium seats. You can get a glass of wine too if you want. ”
15 locals recommend
Café
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“Cool, eclectic, spacious atmosphere. They serve organic, locally sourced food from until 2pm & coffee beverages until close. Definitely a staple of Pittsfield food/coffee culture.”
9 locals recommend
Bar
“Rustic-chic tapas bar with loungy vibe features Spanish small plates, Iberian wines & live musicians.”
12 locals recommend
Pub
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“Great Atmosphere Amazing food, reasonable prices, Great for date night or a family dinner.”
5 locals recommend
Bar
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“Rustic-chic eatery & lounge serving organic wines & craft beer paired with local New American fare. Such a cool, bumping, bar atmosphere. You can dress fancy & not feel out of place. Open late.”
9 locals recommend
Museum
“The family home & garden of Herman Melville in Pittsfield. It's where he wrote Moby Dick while inspired by the view of imposing Mt. Greylock. A substantive stop for fans of history and literature.”
8 locals recommend
Bistro
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“A popular dinner spot in Pittsfield. I had the pan roasted salmon with grilled fennel and risotto and have to admit it was really good. Joe had the burger and adored it. Open every day 4 pm to midnight.”
7 locals recommend
Park
“Drive up to the trail at the forested peak separating New Lebanon from Pittsfield, MA, for a walk and a breathtaking valley view. The road up isn't accessible in winter, but when you can get up there, Berry Pond is lovely for a swim near the top. There's acres of flowering azaleas up there in the third week of June.”
6 locals recommend
Pharmacy
“Groceries nearby - we should have included a discount card there, or just ask for the store card!”
3 locals recommend
Restaurant
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“An upscale northern Italian restaurant in Pittsfield, including an urban outdoor courtyard for when the weather is warm. This is a good place to go for a special occasion; the food is good enough and the place special enough to warrant it without being over the top.”
6 locals recommend
Natural Feature
“City park. Great for swimming and picnicking. Canoe, kayak, and motor boat rentals available on the lake. Surrounded by incredible views of mountains. Live music on the lake every Wednesday night from 5pm-8pm. Free.”
6 locals recommend