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Pittsfield is the largest city in Berkshire County, with about 43,000 people, set in a valley of western Massachusetts between the Taconic Range and the Berkshire hills. Settled in the 1750s, it grew into an industrial city of woolen mills and later a major General Electric center, and a 1791 town bylaw found here contains one of the earliest known written references to baseball.
The city is a gateway to the cultural Berkshires. Herman Melville wrote Moby-Dick at Arrowhead, his farmhouse on the edge of town, and Hancock Shaker Village preserves a 19th-century Shaker community with its famous round stone barn. Downtown, around Park Square, the restored Colonial Theatre, Barrington Stage Company and the Berkshire Museum keep the arts calendar full.
Nature is never far away. Pittsfield State Forest offers trails, wild azaleas and Berry Pond, Onota Lake is popular for swimming and boating, Canoe Meadows Wildlife Sanctuary protects river meadows, and Bousquet Mountain has skiing in winter. Summer evenings bring baseball at historic Wahconah Park.
A living history museum on the site of a Shaker community founded in the 1780s, with 20 historic buildings including the famous 1826 Round Stone Barn, gardens, farm animals and craft demonstrations. Plan at least half a day. It is open seasonally, with spring baby animal days that are popular with families.
The 18th-century farmhouse where Herman Melville lived from 1850 to 1863 and wrote Moby-Dick, gazing from his study window at Mount Greylock. Guided tours show his study, the barn and the grounds, run by the Berkshire County Historical Society. Open seasonally; check tour times.
A museum on South Street founded in 1903 by Zenas Crane, combining art, natural history and science, with a small aquarium, fossils, local wildlife exhibits and hands-on displays for children. It is a good rainy-day stop for families. Allow about two hours, and check for special exhibitions.
A grand 1903 theater on South Street, restored in 2006 and now run by Berkshire Theatre Group, with an ornate gilded interior, balconies and boxes. It presents musicals, concerts, comedy and holiday shows. Even if you are not seeing a show, the lobby and facade are worth a look.
A respected professional theater company based in downtown Pittsfield, staging new plays, musicals and classics on several stages, mostly from late spring to fall. Several of its productions have gone on to Broadway. Book ahead in summer, and pair a show with dinner on North Street.
The historic heart of Pittsfield, an oval green at the meeting of North, South, East and West streets, surrounded by 19th-century buildings, churches and the old Athenaeum. North Street leading off it has restaurants, cafes and galleries. A good starting point for exploring downtown on foot.
A classic ballpark with a wooden grandstand from 1950 where summer collegiate baseball is played. Because home plate faces west, games sometimes pause for a sun delay at dusk. Tickets are inexpensive and the atmosphere is old-fashioned and friendly. Check the summer schedule before you go.
A small, family-friendly ski area on the south side of Pittsfield, opened in the 1930s, with beginner and intermediate trails, night skiing and snow tubing. Lift tickets are cheaper than at bigger resorts. In warmer months it hosts outdoor activities and events; check what is open.
A large state forest on the western edge of the city with hiking trails, campgrounds and a scenic road to Berry Pond, one of the highest natural ponds in Massachusetts. In June, fields of wild azaleas bloom near the summit. Trails range from easy to steep; bring a map.
The largest lake in Pittsfield, with Burbank Park on its eastern shore offering a swimming beach, picnic areas, a boat launch and walking trails. It is popular for fishing, kayaking and sunset views over the hills. Busy on hot summer weekends, so arrive early to find parking.
A Mass Audubon sanctuary along the Housatonic River with easy trails through meadows, woodland, ponds and wetlands. It is good for birding, beaver signs and quiet walks. Trails are flat and family friendly; there is a small fee for non-members.
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