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Unique Free Things to Do in Pittsfield, MA

Free Things to Do in Pittsfield, MA - Downtown Pittsfield
Tracy Givens
Tracy Givens
October 20, 2022

Are you looking for free things to do in Pittsfield, MA? You're in luck—the area is lovely, and most of its pleasures are as easy on the wallet as they are on the eyes. Let's explore the possibilities.

While the Pittsfield region has an undeniably artsy vibe, the Berkshires are replete with opportunities to enjoy family-friendly activities. Visit the Pittsfield Skate Park, completely renovated in 2020 and now boasts plenty of obstacles, ramps, and rails to keep thrill-seekers occupied. Just be sure to use the trash barrels while you're there to keep them clean for the next guests.

Clapp Park

Clapp Park is one of those rare destinations that's enticing no matter the season. Kids can romp on the jungle gym or cool off on the splash pad in summer. Enjoy the athletic fields in the spring and fall, when the weather is cooler. During the winter months, sledding is a popular activity here.

Does your family enjoy paddling and fishing? Visit the 500-acre Pontoonsuc Lake, conveniently located between Pittsfield and Lanesborough. Take your canoe on a leisurely aquatic tour, avoiding the many speedboats that arrive in droves during the warmer months.

In the heart of Pittsfield lies the Pittsfield Common, which is home to the famed Farmers Market. But even if you're not seeking fresh produce or other local products, there are many reasons to drop in on this vibrant green space. Check out the splash pad, the playground, or the basketball court, or relax in the gazebo while sipping a cold beverage. On select nights, there may even be movies or simulcasts on offer.


If you're in the mood for a more strenuous activity, head to Pittsfield State Forest. The area contains 30 miles of hiking and biking trails and 65 acres of azalea fields. It's also home to numerous streams and waterfalls, so keep your camera at the ready.

Just off Dalton Avenue, you'll find another opportunity to work your leg muscles. Despite the trailhead's inglorious location behind a Taco Bell, the hardwood forest known as "The Boulders" offers some gorgeous scenery. It's also a fairly easy trail—just 1.4 miles of leafy ferns and tall trees separate the trailhead from the namesake boulders. Plus, it's dog-friendly if you're looking for tips for traveling to Massachusetts with pets.

Is the weather being uncooperative? Your young bibliophiles will love the Herman Melville Memorial Room, a haven within the Pittsfield Public Library. The space is dedicated to the famed Moby Dick author, containing memorabilia such as family letters, manuscripts, and prized first editions.

Hancock Shaker Village

For a dose of history, check out Hancock Shaker Village. This unique experience offers access to 20 historic buildings, all nestled comfortably within a working heritage farm. You can watch as traditional crafts are brought to life or try crafting yourself. The village also offers musical presentations and other reenactments.

Should you visit on a Sunday in September or October, consider taking in a show at South Mountain's Concert Hall. This venue has featured traditional chamber music for over a century—something the whole family can enjoy together.

One thing is certain: When you and your family stay with us, you won't need to look far to find free things to do in Pittsfield, MA.