9 Best Things to Do in Pittsfield, Massachusetts 

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Massachusetts is a New England state filled with history and natural beauty. Head to the western part of the Bay State and you’ll find the Berkshires, a beautiful, mountainous region that’s a popular vacation spot for many. If you’re taking a trip in the Berkshires, be sure to visit the largest city in Berkshire County: Pittsfield. 

Pittsfield is a city with a population of nearly 44,000 people and plenty of activities to do, from visiting museums to taking in a local show. If you’re interested in taking a day trip sometime soon, here are the best things to do in Pittsfield Massachusetts. 

Aerial view of a city with skyscrapers, church, parking lots and other buildings with a background of mountain ranges in the distance.

Visit the Berkshire Museum 

Address: 39 South Street 

Hours: Monday through Saturday, 10 a.m. to 5 p.m.; Sunday, 12 p.m. to 5 p.m. 

One of the best things to do in Pittsfield is visit the Berkshire Museum, where you’ll be immersed in the worlds of art, natural history, and ancient civilizations. There’s a little bit of something for everyone at the museum, making it a great place to bring the whole family.

Some of the current exhibits you can check out include The Rocks and Minerals Gallery, Objects and Their Stories, and Animals of the World in Miniature. The museum also hosts fun and educational events year-round. 

Children ages 3 and under can visit the museum free; children ages 4 to 17 can get in for $8, and it’s $15 for adult admission. It’s also a good idea to make an online reservation ahead of time so you can get it without an issue. Get ready to have a ball while learning something new! 

Hike in Pittsfield State Forest 

A path through the woods on a sunny day.

Address: 1041 Cascade Street 

Hours: Sunday through Saturday, 6:30 a.m. to 7 p.m. 

Looking to get lost in nature for a bit during your trip to Pittsfield? Head to Pittsfield State Forest for a wonderful and refreshing hike. The 11,000-acre forest has 30 miles of trails you can hike, run, or bike along.

The trails have different difficulty levels, so you can pick a trail that’s best for you. Tranquility Trail, for instance, is only a little more than a half mile long and is considered easy to hike, whereas Turner Trail is more than 5 miles long and is considered moderate to hike. 

You can do other activities in Pittsfield State Forest, like fishing, canoeing, and cross-country skiing. There are also plenty of campsites where you can set up a tent and spend time in the great outdoors. If you can, try to set up a campsite at the top of Berry Mountain; you’ll love the view! 

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Catch a show at Colonial Theatre 

Address: 111 South Street 

Ticket Office Hours: Tuesday through Sunday, 12 p.m. to 5 p.m.; closed Monday; open 12 p.m. to curtain on performance days 

Take in a local show at the Colonial Theatre while visiting Pittsfield. It was built in 1903 and has hosted nearly 120 years of live performances. The well-reviewed Berkshire Theatre Group performs at the Colonial Theatre, along with musical acts.

You can see when the performances will be by checking out the theatre’s full calendar. It’s a great place to go if you’re looking for local art and entertainment in the Berkshires. Book your tickets in advance so you’ll secure your spot during your Pittsfield trip. 

Visit Hancock Shaker Village

A light grey brick round building on the left, a tan building with a brown sloped roof on the right. In front of the buildings there is a wooden fence and a flock of white sheep.

Address: 1843 West Housatonic Street

Hours: Friday through Sunday, 11 a.m. to 4 p.m. 

Step back in time while in Pittsfield by visiting Hancock Shaker Village, a 750-acre space filled with 20 historic Shaker buildings. The village’s mission is to preserve the Shaker lifestyle and bring the story of the Shakers (who came to America in the 18th century) to life. According to its website, it’s the most comprehensively interpreted Shaker site in the world and the oldest working farm in the Berkshires. 

There’s plenty to see at Hancock Shaker Village, including more than 22,000 Shaker artifacts, including furniture, crafts, and pieces of art. You can also see gardens, exhibits, galleries, and replicas of actual Shaker rooms.

There’s also an option to hike along trails in the village, where you can take in the beauty of the Berkshires. Hancock Shaker Village is a unique, educational, and fascinating place to visit in Pittsfield, and it’s an experience you won’t soon forget. 

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Hit the slopes at Bousquet Mountain

Skier in blue going downhill in a cloud of snow

Address: 101 Dan Fox Drive

Hours: See website for seasonal hours 

Skiers and snowboarders, rejoice! Pittsfield has a place where you can enjoy your favorite winter activities. Bousquet Mountain is a 200-acre ski area on the northern summit of Yokun Ridge within the Taconic Mountain Range. Fun fact: it was the first ski area in the United States to offer night skiing! 

Once you arrive, you have your choice of 23 trails to go down. These trails range in difficulty ( from beginner to expert), making it a perfect place to bring skiers and snowboarders of all ages and levels. If you don’t have the equipment you need to enjoy the slopes, don’t worry—you can rent things like skis, boots, poles, snowboards, and helmets.

And if you aren’t into snowboarding or skiing, you can tube instead. No matter what you do, you’ll have a blast and look forward to hitting the slopes again ASAP. 

Visit Arrowhead 

Yellow 2 story house with brown trim, several windows, and grass in front
Editorial credit: LEE SNIDER PHOTO IMAGES / Shutterstock.com

Address: 780 Holmes Road

Hours: Vary by season, see website for seasonal hours 

Arrowhead, also known as the Herman Melville House, is a historic spot in Pittsfield you have to see. It was the home of author Herman Melville from 1850 to 1863, and it’s actually the place he called home when he wrote Moby Dick. You can walk through it and see how the Melville family lived their lives in the Berkshires.

You’ll walk through the home and see what Melville saw while he was writing a classic American novel. The home is designated as a National Historic Landmark and is run by the Berkshire County Historical Society. Take a tour and see a piece of history! 

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See downtown art

Location: Downtown Pittsfield 

One of the coolest things about Pittsfield is that you can walk downtown and see some beautiful artwork. Artscape, a volunteer-led committee, oversees this public exhibit and promotes art throughout the Cultural District. Take a walk downtown to see gorgeous outdoor sculptures and murals—and don’t forget to bring a camera to take plenty of pictures. 

Check out Lake Onota 

3 sailboats in a row on a lake with mountains and green trees in the background

Launch Address: 309 Lakeway Drive

You don’t have to leave Pittsfield to get some nice views of the water. Lake Onota is a 617-acre pond in Pittsfield where you can boat, swim, and fish. The pond has numerous fish populations in it, including Northern Pike, Rainbow Smelt and, occasionally, White Catfish.

It’s a great spot to stroll along while admiring the natural beauty of the Berkshires. Head there in the summer to enjoy some fun water activities and catch some sun. 

Visit Guido’s Fresh Marketplace 

Address: 1020 South Street

Hours: Monday through Saturday, 9 a.m. to 7 p.m.; Sunday, 10 a.m. to 6 p.m. 

There’s nothing like stopping into a local establishment and seeing what it serves the community. When you’re in Pittsfield, make sure to stop by Guido’s Fresh Marketplace on South Street to pick up some delicious food. This family-owned marketplace has fresh produce and quality prepared foods for you to pick up during your trip. Stop into the market and see all it has to offer. 

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