Things to Do in Pittsfield MA — Bucket List

NOTE: As the state releases new guidelines, please practice social distancing guidelines and know that we try to keep these lists as updated as possible. Many sites and venues will not be opening for the summer so please call ahead before going. If you see a change please email kellym@macaronikid.com.

• Enjoy a house tour of the restored home of famed Moby Dick author Herman Melville (Admission Fee) or opt for a self-guided tour of the grounds (Free) at Arrowhead, Pittsfield.
• Catch a family-friendly play or musical at Barrington Stage Company, Pittsfield, the local theater company with a primary focus of bringing more young people to the theater, offering educational programs, playwright mentoring, and the “KidsAct” summer program.
• You will have to tear your kids away from the Spark Creativity Lab if you want to see all the at Berkshire Museum, Pittsfield — the Hall of Innovation (with kid-friendly craft area), aquarium, theater, rotating exhibits, and natural history and art installations. (Kids under 3 FREE)
• Head to Bousquet Mountain, Pittsfield for a day of adventure year round — 200 acres of downhill skiing on the Yukon Ridge. 2 terrain parks, 23 trails, 3 double lifts, 2 carpet lifts, water slides, play a round of disc golf or explore the Adventure Park.
• Hike the trails, take in a free program or tour the gardens at Canoe Meadows, Pittsfield, located along the banks of the Housatonic River, Holmes Road, Pittsfield. (FREE; donations accepted.)
• Catch an outdoor family flick at Clapp Park, Pittsfield, one of the largest play structures in the county, playing fields, running/walking track (8 laps = 5 miles), and a spectacularly steep sledding hill. Check out Clapp Park’s Summer 2015 Outdoor Movie Schedule HERE.
• Schedule a playdate and picnic at the newly renovated First Street Common, Pittsfield, equipped with a pavilion, bathrooms, basketball court, gazebo, new play structure, and a splash park (coming this summer) in an urban downtown setting. (FREE)
• Spend a day exploring Hancock Shaker Village, Pittsfield, a 750-acre living-history museum, that boasts twenty historically authentic buildings, heirloom gardens, livestock barn and pastures, and 1-mile Farm & Forest Trail. In the Discovery Room, kids can learn about farming, dress like a Shaker, make a craft to bring home, and even try their hand at milking a cow (replica). (Children 12 and under FREE.)
• Stop for a fresh snack (pick your own blueberries or raspberries) at Kirchner’s Farm, Pittsfield.
• Rent a boat for the day at Pontoosuc Lake, Pittsfield/Lanesborough and spend the day tubing or waterskiing in this beautiful 480-acre lake.
• Explore over 30 miles of Taconic Mountain Range trails or fish at 2,150-feet above sea level, in Berry Pond, one of the highest bodies of water in Massachusetts at the Pittsfield State Forest, Pittsfield. Swimming and picnicking are also available in the natural cold spring pool at LuLu Brook.
• Explore over 30 miles of Taconic Mountain Range trails or fish at 2,150-feet above sea level, in Berry Pond, one of the highest bodies of water in Massachusetts at the Pittsfield State Forest, Pittsfield. Swimming and picnicking are also available in the natural cold spring pool at LuLu Brook.
• Get festive at one of the regions award-winning Fourth of July Parade in Pittsfield (FREE)
• Take in a performance at The Colonial Theatre. Performances range from family-friendly community theater, concerts, comedians, smaller musical performances in The Garage, the annual Holiday Extravaganza, and more.
• Enjoy a round of disc golf at Kirvin Park (Sackett Brook), Pittsfield, surrounded by plenty of running room on soccer fields, swings, and a fun play structure. (FREE)
• Hike, ski, snowshoe, run, mountain bike, hunt, fish, forage, nature watch, paint pictures, take photographs, eat and drink, walk your dog off-leash, hunt for geocaches, nap or get married at the Mahanna Cobble, Lenox/Pittsfield. (FREE)
• Attend a Pittsfield Suns ballgame or a free summer concert at Wahconah Park, Pittsfield, one of the country’s only remaining ballparks with a wooden grandstand.