Guidebook for Pittsfield
Food Scene
Excellent cocktails and small-menu dinner on West Street. Small, intimate space.
54 locals recommend
District Kitchen & Bar
40 West StExcellent cocktails and small-menu dinner on West Street. Small, intimate space.
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.
11 locals recommend
Hotel on North
297 North StOccasional 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.
Great espresso drinks, delicious breakfast and lunch selections.
17 locals recommend
The Marketplace Cafe
53 North StGreat espresso drinks, delicious breakfast and lunch selections.
Cafe and traditional sourdough bakery, as seen on Netflix's Cooked. Incredible breads, PIZZA, and sandwiches as well as coffee, pesto for purchase, and much more. Highly recommended.
19 locals recommend
Berkshire Mountain Bakery Pizza Cafe
180 Elm StCafe and traditional sourdough bakery, as seen on Netflix's Cooked. Incredible breads, PIZZA, and sandwiches as well as coffee, pesto for purchase, and much more. Highly recommended.
Awesome beers on tap, and the best wings around. Pretty views from seating area on the deck. Salad bar.
39 locals recommend
Olde Forge Restaurant
125 N Main StAwesome beers on tap, and the best wings around. Pretty views from seating area on the deck. Salad bar.
Drinks & Nightlife
Great food served until midnight on the weekends, live music, good beers (local beers on tap) and overall fun atmosphere.
36 locals recommend
Mission
438 North StGreat food served until midnight on the weekends, live music, good beers (local beers on tap) and overall fun atmosphere.
Methuselah
391 North StreetGreat wine and selection of cocktails.
Thistle & Mirth
44 West StGreat beers, fun atmosphere, bring your own food.
Parks & Nature
Wildlife sanctuary with a mix of short/beautiful walks through native trees and plants and moderate to semi-strenuous hike to the top f the mountain with views over Hancock and into the eastern New York hill towns. $5 entry.
Pleasant Valley
Wildlife sanctuary with a mix of short/beautiful walks through native trees and plants and moderate to semi-strenuous hike to the top f the mountain with views over Hancock and into the eastern New York hill towns. $5 entry.
Beautiful walks through native plants and sightings of wildlife. no entry fee.
21 locals recommend
Mass Audubon Canoe Meadows Wildlife Sanctuary
309 Holmes RdBeautiful walks through native plants and sightings of wildlife. no entry fee.
Excellent for sight-seeing and hiking, biking, and snow-shoeing. incredible views at the top of the mountain span from Hudson New York on the right to the Adirondack mountains on the left. Picnic areas throughout and at the top of the mountain.
44 locals recommend
Pittsfield State Forest
1041 Cascade StExcellent for sight-seeing and hiking, biking, and snow-shoeing. incredible views at the top of the mountain span from Hudson New York on the right to the Adirondack mountains on the left. Picnic areas throughout and at the top of the mountain.
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.
37 locals recommend
Onota Lake
Lakeway DriveCity 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.
Arts & Culture
Colonial Theatre
111 South StBeautiful theater with music and plays.
Berkshire Museum
39 South StArts and history. Great place to visit with children!
Traditional Shaker village. Tours available. Open daily from 10am-4pm. Beautiful surrounding property.
161 locals recommend
Hancock Shaker Village
1843 W Housatonic StTraditional Shaker village. Tours available. Open daily from 10am-4pm. Beautiful surrounding property.
Edith Warton's home built in the early 1900's. I would recommend the home and garden tours. Local art throughout grounds. Live, free music offered weekly that is bring your own picnic and BYOB.
167 locals recommend
The Mount, Edith Wharton's Home
2 Plunkett StEdith Warton's home built in the early 1900's. I would recommend the home and garden tours. Local art throughout grounds. Live, free music offered weekly that is bring your own picnic and BYOB.
Essentials
Fresh local produce available when in season. Really great butcher, cheese selection, and wine.
248 locals recommend
Guido's Fresh Marketplace
760 S Main StFresh local produce available when in season. Really great butcher, cheese selection, and wine.
Entertainment & Activities
Old, pretty theater showing yearly film festival and blockbusters. Beer, wine, and snacks available for purchase.
44 locals recommend
Phoenix Theatres Beacon Cinema
57 North StOld, pretty theater showing yearly film festival and blockbusters. Beer, wine, and snacks available for purchase.