Top 12 Best Things to Do in Pittsfield Massachusetts

You’ll find plenty of things to do in Pittsfield MA, including wandering through the historic downtown, exploring a living history museum, and partaking in numerous outdoor adventures.

An aerial view of Pittsfield MA

Pittsfield, the largest city in Berkshire County with approximately 44,000 residents, offers a variety of activities and attractions for any visitor.

While not a top Berkshire destination in the same way Lenox, Stockbridge, Williamstown, or Great Barrington are, you’ll still find a mix of cultural, outdoor, and recreational activities here that cater to different interests.

Anyone driving from north to south or vice versa in the Berkshires is likely to pass through Pittsfield. Rather than drive through, look at some of the attractions Pittsfield offers. Whether you’re into history, arts, nature, or entertainment, Pittsfield has something for everyone.

Here are the top things to do in Pittsfield MA.

Explore the Berkshire Museum

One of the main attractions in Pittsfield is the Berkshire Museum, which features exhibits on natural history, art, and science.

Founded in 1903, the Berkshire Museum’s original mission was to blend the best attributes of the American Museum of Natural History, the Smithsonian, and the Metropolitan Museum of Art to provide a “window into the world” for the people of Western Massachusetts.

Today, that legacy lives on in the museum’s wide variety of exhibits, such as Animals of the World in MiniatureThe Hall of Innovation, and The Rocks and Minerals Gallery.

One unique feature of the Berkshire Museum is its aquarium, which has more than 35 tanks that include tropical and freshwater fish, reptiles, amphibians, and more.

The museum is open Monday – Saturday from 10 AM – 5 PM and Sunday from 12 PM to 5 PM. Admission is $15 for adults and $8 for children ages 4 – 17. (Check the website to confirm times and prices) (39 South Street)

Catch a show with the Barrington Stage Company

Another top attraction and among the best things to do in Pittsfield MA is to catch a show at the Barrington Stage Company.

This theater production company claims it’s the fastest-growing arts venue in Berkshire County. It attracts more than 57,500 visitors annually. There are three performance venues to see a Barrington Stage Company show, all located in downtown Pittsfield.

You’ll find various productions from this company, including contemporary and classic plays, musical theater, off-Broadway and regional theater transfers, and new works and world premiers, among others.

Tickets can be purchased online or at the box office at 30 Union Street in Pittsfield.

Wander through the Hancock Shaker Village

Buildings at the Hancock Shaker Village in Pittsfield MA

Step into a living history museum with a visit to the Hancock Shaker Village located on the outskirts of Pittsfield.

The Shakers, a religious group, gathered in Hancock in the early 1780s, many having arrived from England only years earlier. For over 170 years, the Shakers called this village their home until their numbers dwindled. In 1960, a non-profit took over the property to preserve the village for future generations.

This historic site showcases Shaker architecture, lifestyle, and culture, including 20 buildings and multiple acres of gardens and walking trails. You can take a self-guided tour of the property, and families with kids will want to stop in the hands-on discovery room that includes crafts and the ability to dress like a Shaker.

The Shaker Hancock Village is open in the spring, summer, and fall every day from 10 AM to 5 PM. Admission for adults is $20 and $8 for children, with special discounts given to select individuals. (Check the website to confirm times and prices) (1843 West Housatonic Street)

Enjoy the outdoors at Pittsfield State Forest

Outdoor enthusiasts will find several outdoor activities to explore within the Pittsfield State Forest.

This expansive 11,000-acre forest offers hiking and biking trails, picnic areas, fishing opportunities, and the ability to canoe, kayak, and swim. In the winter, it’s possible to cross-country ski and snowmobile along some of the forest’s trails.

Hiking is popular here with picturesque trails such as the Shaker Mountain Loop or Berry Pond Trail. A few trails lead up to summit views on top of Berry Mountain. Click here for a trail map.

Camping is also available onsite for both tents and RVs. And it’s even possible to pitch a tent on top of the mountain, although the site is more rustic.

Daily parking fees are in effect between the middle of May and Labor Day – $5 for Massachusetts residents and $20 for non-Massachusetts residents. (Check the website to confirm times and prices) (1041 Cascade Street)

Watch a performance at the Colonial Theatre

Among the best artistic things to do in Pittsfield MA is to catch a performance at the Colonial Theatre, a beautifully restored historic venue in downtown Pittsfield.

The Colonial Theatre hosts a variety of live performances, including concerts, plays, and dance shows put on by the Berkshire Theater Group. The Group has two additional stages, The Unicorn Theatre and The Fitzpatrick Main Stage in nearby Stockbridge.

Check the website to see which shows are available while you’re visiting. Tickets can be purchased online or at the box office. (111 South Street)

Spend time on Onota Lake

Onota Lake on a foggy day - one of the things to do in Pittsfield MA

Another way to get outside during your visit to Pittsfield is to spend time at Onota Lake.

This 617-acre freshwater lake is owned and managed by the city. Visitors can enjoy swimming on Ramsey Beach, boating, fishing, or relaxing on the shore.

The lake is in the northwest corner of the city. Ramsey Beach can be reached via Lakeway Drive.

Wander through art galleries and studios

A blurry image of people looking at art in an art gallery

As the biggest city in the Berkshires – a region known for its spectacular arts community – unsurprisingly, Pittsfield has several art galleries and artist studios to visit.

Wandering through the downtown area, you’ll discover unique artwork, sculptures, and crafts created by talented local artists.

Here are a few galleries to put on your list:

Explore the teen-run Pittsfield Farmers Market

Produce showcased at a farmer's market

Check out the Pittsfield Farmers Market if you’re in town during warmer months.

Browse through fresh produce, local products, baked goods, and artisanal products, and enjoy live music and community events.

You can also see live chef demos, partake in workshops, and get your kids involved in children’s activities. Of note – this is the region’s first teen-run farmer’s market.

Held on Saturdays during the summer and fall from 9 AM – 1 PM. (Check the website to confirm times and location) (Pittsfield Common, 100 First Street)

Catch a game with the Pittsfield Suns

A bat, mit, and a baseball placed over a base - clearly on a baseball field

One of the best things to do in Pittsfield MA for sports enthusiasts is to catch a Suns baseball game at Wahconah Park.

This summer collegiate baseball team plays over 50 games yearly with a few post-season appearances.

See the website to view the summer roaster and purchase tickets. (105 Wahconah Street)

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Enjoy outdoor recreation at Pontoosuc Lake

Another lake you’ll want to add to your list while in Pittsfield is the Pontoosuc, located on the northern edge of the city and shared with the town of Lanesborough.

Outdoor activities on the lake include boating, water skiing, fishing, swimming, and picnicking.

There are also numerous vacation rentals along the shores, making Pontoosuc a popular and busy place in the summertime. In total, the lake is 480 acres. (North Street and Hancock Road)

Tour Arrowhead and see how Herman Melville lived

Arrowhead the former home of Herman Melville - among the best things to do in the Berkshires
Photo credit: Daderot / Creative Commons

Bibliophiles will want to make extra room in their itinerary to visit Arrowhead, the former home of Herman Melville and where he wrote Moby Dick.

This historic site offers a unique opportunity to step into the world of one of the greatest novelists of the 19th century. Arrowhead was Melville’s residence for many years, where he penned some of his most famous works, including the literary masterpiece “Moby-Dick.”

You’ll gain insights into Melville’s life and creative process as you explore Arrowhead’s grounds and meticulously preserved interior. The site offers a window into the daily life of the author, his family, and the world that inspired his literary genius.

Arrowhead is open from the middle of May to the end of October by guided tour only, Thursday – Monday. Tours are every hour and begin at 10 AM, with the last tour at 3 PM. Adults are $20, and children under 12 are free. (Check the website to verify times and admission prices)

Follow a historical walking tour of the city

Pittsfield was incorporated in 1761, so you can imagine the number of historic buildings within its city limits.

Follow a free self-paced tour to learn more about the city’s rich history, architecture, and notable landmarks.

This website provides free access to the tour. Following the map, you can read information about each building and its significance to the city.

(As a GetYourGuide affiliate, I earn from qualifying purchases at no extra cost to you.)

A photo of Kerry Flatley leaning against a wall

About Kerry Flatley

Kerry Flatley has lived in New England for the past 26 years. She has roots in Maine & Massachusetts, family in New Hampshire, and grew up close to the Connecticut border. She loves all that this region has to offer – the ocean, mountains, islands, history, villages, and cities. When she’s not writing about New England, she’s relaxing at home in the Boston suburbs with her two teenage daughters and husband.

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