- 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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35.7 Miles
US Route 20 is a scenic byway that offers views of the countryside and takes travelers past a variety of antique stores, restaurants, inns, and historic buildings. The natural scenery and historic attractions are its chief attractions.
35.8 Miles
Once a warehouse, the Bridge Street Theatre is a 72-seat proscenium theater offering several productions each season. The lobby of the theater is used for both art exhibitions, workshops and small concerts.
35.9 Miles
Haystack Golf Club is a golf course and club with views of the ridgeline and Haystack Mountains. The course has a traditional layout of 18 holes and requires both soft spike shoes and proper golf attire.
35.9 Miles
Humor-based fine art forms the primary collection in The Art of Humor Gallery. Specifically, the works of artist and cartoonist Skip Marrow are the focus of the collection, including Marrow's watercolor originals, prints, and cards.
35.9 Miles
A riverfront park along the Hudson River, Dutchman's Landing features picnic tables, barbecue pits, a playground and boat launch. The park is located in the Village of Catskill, a town filled with historic buildings, restaurants and shops.
36.2 Miles
Catskill Hoebowl is a bowling alley that features a video game arcade, karaoke nights, comedy nights, a snack par, and billiards tables. The alley is also available for birthday parties and fundraisers.
36.3 Miles
Located in Holyoke, Massachusetts, the Wisteriahurst Museum is an expansive mansion with manicured grounds and a gorgeous atmosphere. It was originally a home, but is now a rentable event facility that is among the region's most coveted wedding venues.
36.4 Miles
Spanning almost 6000 acres, Albany Pine Bush Preserve is a fresh water pine barren with trails for hiking and nature walks. A unique and endangered ecosystem, the Preserve features informative exhibits, as well.
36.4 Miles
With 24-lanes of bowling available to its guests, the Hoebowl Bowling Centers provides fun and entertainment to its guests. Other amenities include a snack bar, pro shop, game arcade, and lounge.