Pittsfield, Berkshire County, MA
Places to go in Pittsfield
49 scouted venues — the coffee shops, restaurants, parks, and hidden corners we think are worth your time.
Outdoors
Monument Mountain
Mountain park with an Indian monument, hiking trails, skiing, hunting, picnicking & birding.
US-7, Great Barrington, MA 01230, USA
Outdoors
Mount Greylock State Reservation
With hiking & a summit road in season, the highest point in the state offers 60- to 90-mile views.
30 Rockwell Rd, Lanesborough, MA 01237, USA
Outdoors
Natural Bridge State Park
An abandoned marble quarry with a naturally formed arch & a man-made dam, both of white marble.
McAuley Rd, North Adams, MA 01247, USA
Arts & Culture
Naumkeag
Visitors can tour this spacious, 19th-century summer home & picnic on its landscaped grounds.
5 Prospect Hill Rd, Stockbridge, MA 01262, USA
Food & Drink
No. Six Depot Roastery & Cafe
House-roasted coffee & simple fare served in a rustic-chic cafe with a gallery of local art.
6 Depot St, West Stockbridge, MA 01266, USA
Arts & Culture
Norman Rockwell Museum
Significant collection of the artist's original work & memorabilia on display in his hometown.
9 Glendale Rd, Stockbridge, MA 01262, USA
Outdoors
October Mountain State Forest
Home to the famed Appalachian Trail, this expansive forest offers camping, hiking & a fishing lake.
317 Woodland Rd, Lee, MA 01238, USA
Sports & Recreation
Olivia's Overlook at Yokun Ridge Reserve
Yokun Ridge South Hiking Trails, South Dr, West Stockbridge, MA 01266, USA
Food & Drink
Otto's Kitchen & Comfort
Hearty American breakfast, lunch & dinner served in a relaxed dining room with big front windows.
95 East St, Pittsfield, MA 01201, USA
Food & Drink
Patrick's Pub
Irish-style bar offering hearty American pub eats & brews on tap in a cozy, wood-&-brick setting.
26 Bank Row, Pittsfield, MA 01201, USA
Food & Drink
Proprietor's Lodge
22 Waubeek Rd, Pittsfield, MA 01201, USA
Food & Drink
RARE 297 Steakhouse
297 North St, Pittsfield, MA 01201, USA
Food & Drink
RJ'S RESTAURANT SEAFOOD/CHOPS/PASTA
109 First St, Pittsfield, MA 01201, USA
Food & Drink
Roasted Garlic
Quaint family-owned eatery dishing up wood-fired pizzas, burgers, pastas & sandwiches.
483 W Housatonic St, Pittsfield, MA 01201, USA
Food & Drink
Sibaritas Restaurant Inc
27 Mc Kay St, Pittsfield, MA 01201, USA
Shopping
T.J. Maxx
Discount retail chain featuring stylish brand-name apparel, shoes & accessories, plus housewares.
690 Merrill Rd, Pittsfield, MA 01201, USA
Arts & Culture
Tanglewood
297 West St, Lenox, MA 01240, USA
Shopping
The Center at Lenox
489 Pittsfield Rd, Lenox, MA 01240, USA
Arts & Culture
The Colonial Theatre: Berkshire Theatre Group
Opulent historic 760-seat space, part of the Berkshire Theatre Group, presents plays, music & dance.
111 South St, Pittsfield, MA 01201, USA
Outdoors
The Common
100 First St, Pittsfield, MA 01201, USA
Arts & Culture
The Mount, Edith Wharton Cultural Center
Author Edith Wharton's turn-of-the-century estate offers tours & hosts frequent cultural events.
2 Plunkett St, Lenox, MA 01240, USA
Arts & Culture
Ventfort Hall Gilded Age Mansion & Museum
Restored, listed Jacobean revival mansion built in 1893 & open for tours & events.
104 Walker St, Lenox, MA 01240, USA
Outdoors
Wahconah Falls State Park
48-acre wooded state park with waterfalls, picnic areas & hiking trails, plus fishing & restrooms.
68 Wahconah Falls Rd, Dalton, MA 01226, USA
Sports & Recreation
Wyndhurst Golf & Club
High-end rooms & suites on 380 acres, plus numerous sports facilities & dining options.
55 Lee Rd, Lenox, MA 01240, USA