Pittsfield, Massachusetts, is a small town in the northwest part of the state. Despite its small size, it’s the largest city in Berkshire County and is a fantastic place to visit. Whether visiting Pittsfield as a family, with friends, or as a romantic getaway, you will be in awe of the city’s beauty!
The former mill town is a close weekend destination for many, including those from Boston, New York, Jersey City, Newark, Philadelphia, and Montreal. Pittsfield has it all if you’re looking for four-season recreation, world-class theaters, excellent museums, and delectable dining!
In addition, the city is pedestrian-friendly, with many attractions within walking distance.Families will enjoy the interactive exhibits at the first-class Berkshire Museum, the oldest working farm at Hancock Shaker Village, and the Tranquility Trail at Pittsfield State Forest.
In addition, families flock to Burbank Park at Lake Onota during the summer to swim, kayak, or ride a pontoon boat. For outdoor adventurers, Pittsfield has year-round outdoor recreation, including hiking trails at Pittsfield State Forest (and snowshoeing trails in the winter!), skiing and tubing at Bousquet Mountain, hiking and cross-country skiing at Springside Park, and fishing at Lake Onota.
Couples will find many fun things to do, including a trip to Lake Onota, dinner at District Kitchen & Bar, one of the live performances at the Colonial Theatre, and a nightcap at Methuselah Bar and Lounge.
So, whether you’re visiting Pittsfield with your significant other, friends, or children, you’ll find many amazing things to do in Pittsfield, Massachusetts!
TLDR
- Most significant landmark – Hancock Shaker Village
- Best park – Springside Park
- Best free activity – Canoe Meadows Wildlife Sanctuary
- Best activity for kids – Bousquet Ski Area/Play Bousquet
- Best activity for adults – The Colonial Theatre
- Best food – District Kitchen and Bar
- Best nightlife – Methuselah Bar & Lounge
- Best all-around accommodation – Berkshire Mountain Lodge
Best & Fun Things to Do in Pittsfield, Massachusetts
1. Pittsfield State Forest
Address: 1041 Cascade St, Pittsfield, MA 01201
Pittsfield State Forest is a year-round destination for outdoor lovers, with 30 miles of trails for hiking, mountain biking, horseback riding, and cross-country skiing. The state park includes 11,000 acres, numerous campsites, cascading streams, and Pontoosuc Lake.
The trails range from novice…
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