- 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
Kennedy Park is a park known for its multiple hiking and mountain biking trails of various difficulty levels. Attractions include hiking, mountain biking, horseback riding, picnicking, and cross country skiing.
With trails going through the surrounding hills and mountains, Aspinwall Equestrian Center lead horseback rides for riders of all skill levels. Before the trip, the visitors can learn the basics of horseback riding from experienced instructors.
100% 7 votes
472 W Mountain Road, Lenox, MA 01240 MoreLess Info
Featuring over 1,000 acres of protected land, the Mass Audubon Pleasant Valley Wildlife Sanctuary is a preserve popular among nature lovers. Visitors commonly enjoy hiking through the sanctuary, viewing the native plants and wildlife that call the location home.
Combining the founder's two passions, art and Judaism, Lenox Judaica is a collection and gallery of Jewish inspired artwork and many ceremonial items. Some available items include candles, art, Ellis Island dolls, dreidels, and gifts for Bar and Bat Mitzvahs.
Berkshire Scenic Railway Museum features the restored Lenox Station which dates back to 1903 and houses a number of interactive railroad exhibits which include vintage engines, passenger cars and the Yokun block station.
Constructed in 1815 in the Greek-revival architectural style, the Lenox Library today functions as a reference center with its extensive collection of books on a variety of topics, in addition to the numerous cassettes and videos that make up the music section.
The family owned and operated Berkshire Canoe Tours offers guided canoe trips on the Housatonic River. Guests might see red-tail hawks, owls, Great Blue Heron, painted turtles, or other wildlife in the course of a ninety minute tour.