- Our list of the best things to do in Pittsfield, Massachusetts, features the top 104 nearby activities — including 61 great attractions with user approval ratings of 90% or more!
- Pittsfield, MA has a variety of great sights and experiences nearby. Top categories include: Museums & Galleries, Entertainment & Shows, Outdoor Places, and Sights & Landmarks.
- The results below include the top 18 things to do within the city of Pittsfield, MA , followed by 86 popular activities in nearby cities, including Lenox, North Adams, Williamstown, Great Barrington, Lee, Charlemont, Stockbridge and Ashfield
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47.3 Miles
The beautiful Windsor Dog Park is a third of an acre of sprawling land and includes two play areas, for both large and small breeds. The park allows dogs to run off-leash and features wood chip mulch fenced-in play areas.
47.4 Miles
Visitors to Kent Falls State Park enjoy hiking, biking, picnicking and other fun outdoor pursuits. Park entrance is free, but guests must pay to park between Memorial Day and Labor Day.
47.5 Miles
Teach your kids to ski by taking them to Maple Ski Ridge, where the professional staff caters to young and old beginners alike. Featuring a simple 300-foot vertical drop, newbies won't be overwhelmed by the mountain and can learn at their own pace.
47.5 Miles
Skater City is an indoor amusement facility that features a variety of entertainments. Attractions include roller skating, toxic laser tag, miniature golf, and an extensive video game arcade. The facility hosts birthday parties and special events.
47.6 Miles
Experience Mount Equinox, southern Vermont's highest peak, via the Skyline Drive, with picnic areas and lookouts along its 5.2 mile climb. At the summit, visit the Saint Bruno Scenic Viewing Centre, with information about the Carthusian Monks, whose only US monastery is located on the mountain.
47.6 Miles
Guided tours of Wing Castle and its grounds are available at regular times from Memorial Day to Labor Day. There is also an on-site bed and breakfast that embraces the style and decor of a European fairy tale.
47.6 Miles
Passing through Amherst, Massachusetts, the Metacomet-Monadnock Trail is one of New England's most popular hiking destinations. It is one component of the New England Scenic Trail route. This trail is best hiked in late summer and early autumn.
47.8 Miles
26 Wing Road, Millbrook, NY 12545
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Tours and wine tastings are offered daily at the Millbrook Vineyards & Winery throughout the year. From Memorial Day through October, guests can also visit the Vineyard Grill and Cafe to eat local gourmet food in a large tent near the pond.
47.8 Miles
The Catskill Animal Sanctuary is a 110 acre animal sanctuary for farm animals rescued from animal cruelty. Attractions include a guided tour of the sanctuary, cooking classes, overnight lodging, and various special events.
47.8 Miles
The area known as the Skyline Overlook is found on a part of Hogback Mountain. On a clear day, visitors can enjoy a view of roughly 100 miles in every direction from this high point.