11 Best Things to Do in Pittsfield, Massachusetts

Pittsfield, Massachusetts, is a small town northwest of the state. Despite its small size, it’s the largest city in Berkshire County and is a fantastic place to visit. These are the best things to do in Pittsfield.

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.

TL;DR

• Most significant landmark – Hancock Shaker Village
• Park to visit – Springside Park
• Free activity – Canoe Meadows Wildlife Sanctuary
• Activity for kids – Bousquet Ski Area/Play Bousquet
• Activity for adults – The Colonial Theatre
• Place to eat – District Kitchen and Bar
• Nightlife – Methuselah Bar & Lounge
• Place to stay – Berkshire Mountain Lodge

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 to expert, with the most accessible trail being the Tranquility Trail. If you’re looking for more challenge, try the 11-mile Shaker Village to Parker Pond hike. This hike has an elevation gain of over 2,000 feet and usually takes five hours.

There are three campgrounds: Berry Pond, Parker Brook, and Bishop Field. To stay on top of Berry Mountain, you’ll want one of the 13 campsites in the Berry Pond Campground. Conversely, if you want to pitch a tent at the mountain’s base, grab a spot at the Parker Brook Campground. Lastly, if you prefer open-field campsites, check out Bishop Field Campground.

Summertime activities at the state park include hiking, camping, mountain biking, kayaking, horseback riding, and fishing. Wintertime recreation opportunities include cross-country skiing, snowmobiling, and snowshoeing. With four-season outdoor recreation at Pittsfield State Forest, it’s an ideal destination for nature lovers!

See Related: Things to Do in Massachusetts & Places to Visit

 2. Hancock Shaker Village

Address: 1843 W Housatonic St, Pittsfield, MA 01201

Hancock Shaker Village is among Pittsfield, Massachusetts’s most fascinating and educational. The Village is a former Shaker commune that emerged in the 1780s and was active for almost two centuries.

When it closed in 1960, a non-profit purchased the land and turned it into the open-air museum it is today. 1968 Hancock Shaker Village was added to the National Register of Historic Places and declared a National Historic Landmark District.

Visitors can spend all day learning about Shaker life in the 750-acre Village, with 50 room-setting exhibits, a Shaker Mercantile, and an onsite Cafe. In addition, visitors can also explore many of the property’s trails, pass by abandoned Shaker buildings, and even see the holy site, Mount Sinai.

Not only can you walk through these real-life exhibits with real Shaker furniture, tools, and equipment, but many areas have costumed interpreters that provide a more in-depth learning experience.

For example, one of the many exhibits is an infirmary with hospital beds and 19th-century medical equipment, and another is a Dairy and Weaving Loft with looms, spinning wheels, and butter churns.

Lastly, many visitors hike to the holy site of Mount Sinai from Shaker Village; it is a 2.6-mile round-trip trail that takes you to the North Family sites and then to the sacred site in Pittsfield State Forest.

3. Berkshire Museum

Address: 39 South Street, Pittsfield, MA 01201

The Berkshire Museum is an exceptional educational experience worth the trip from New York, Albany, or Boston. The Museum is more than just art; it includes ancient civilization, science, and natural history.

In partnership with the Smithsonian, the Berkshire Museum is one of the few museums in the United States that can share the Smithsonian’s resources with its visitors. Kids especially love the hands-on exhibits, the aquarium, and the engaging programming.

However, a trip to the Berkshire Museum is fun for all ages! The first floor is an interactive exhibit encompassing over 3,000 square feet.

This exhibition celebrates regional inventors and the inventions that have shaped the world. In addition, many visitors enjoy the Animals of the World in Miniature exhibition, with fourteen different ecosystems displayed in rich, lifelike scenes.

However, young visitors find the Aquarium and Reptile Room one of the best things to explore because they can see reptiles, amphibians, fish, and insects up close! This eclectic museum is one of the best things to do in Pittsfield, Massachusetts, on any given day.

You can also visit the museum shop to take home some mementos and souvenirs to your house or dog sitter! In addition, the convenient location in downtown Pittsfield makes it a perfect place to stop on a rainy day.

See Related: Museums in the US You Need to Visit

4. Pleasant Valley Wildlife Sanctuary

Address: 472 W Mountain Rd, Lenox, MA 01240

Pleasant Valley Wildlife Sanctuary is just a short drive from Pittsfield in the neighboring town of Lenox. This 1,400-acre wildlife sanctuary is part of the Massachusetts Audubon Society and is an excellent place for hiking, bird watching, and wildlife viewing.

In the majestic barn on the property, you can also see works of art by six local artists who share their visions of nature. There are seven miles of hiking trails, with one of the trails heading to Lenox Mountain’s peak.

Regardless of which path you decide to take, you’ll go through various habitats such as wetlands, meadows, forests, and mountains. Because of the different habitats, there is a range of hikes, from easy to challenging. While hiking, you may see beavers, or at least evidence, via dens or dams.

The walking trails include loop trails, boardwalks, and scenic views. If you want to stay in Lenox after spending the day at the sanctuary, the Hampton Inn & Suites Berkshires-Lenox is perfect with its signature Cloud Nine beds, swimming pool, and mountain views.

5. Arrowhead Museum

Address: 780 Holmes Rd, Pittsfield, MA 01201

You’ll find a trip to the Arrowhead Museum very educational. The Herman Melville House, also known as Arrowhead, was the famous author’s home during his most prolific years.

Melville named the farm “Arrowhead” due to the native artifacts he found in the fields. Herman Melville bought the house and barns encompassing 160 acres in 1850. Part of his job was to care for the horse and milk the cows; he also planted tomatoes, corn, potatoes, and apples. 

His life at Arrowhead and the surrounding area inspired many of his stories and novels. Along with Moby Dick, Melville wrote Bartleby, the Scrivener, The Bell Tower, and Israel Potter: His Fifty Years of Exile during his time at Arrowhead. 

Today, it is a historic house museum, with tours of where Herman Melville produced some of his most remarkable work. The Melville Trail also connects many of the author’s most beloved places in Berkshire County with interpretive panels.

Some places on the trail include Pontoosuc Lake, Monument Mountain, Berkshire Athenaeum, Balance Rock, and Mount Greylock. Arrowhead is a great place to learn about Henry Melville and see the inspiration behind his best works. This museum is easily one of the best things to do in Pittsfield, Massachusetts!

If you want to rest your feet and head nearby, consider the Berkshire Mountain Lodge, with a hot tub and game room on site!

6. Colonial Theatre

Address: 111 South Street, Pittsfield, MA 01201

The Colonial Theatre is part of the Berkshire Theatre Group, which manages the Unicorn Theatre and the Fitzpatrick Main Stage. Opened in 1903, the theatre boasted classical architecture and excellent acoustics. Of the 220 theatres architect J.B. McElfatrick designed, the Colonial Theatre is one of six still standing.

After a long and storied history, including the theatre’s closure multiple times (during the Depression and WWII) and the theatre-going to auction, it reopened in 2006 after a $21 million restoration. The renovation preserved the theatre’s historical design while creating a modern performance center.

Today, the theatre has 780 seats and features live performances from national acts such as the legendary country-pop crossover band Lonestar and live music such as the Pittsfield CityJazz Festival and Bennie & The Jets: A Tribute to Elton John.

If you get a chance to visit the Colonial Theatre, you’ll be in awe of the architectural details inside, from the elaborately decorated balcony to the vaulted entrance. The theatre is a wonderful place with a lot of history and is one of the best things to do in Pittsfield, Massachusetts!

Start your evening right before the show with a cocktail and dinner at the nearby District Kitchen & Bar for modern American food in a comfortable setting. If you want a nightcap to end your evening, the Methuselah Bar and Lounge is perfect for a glass of Berkshire Mountain Distillers Berkshire Bourbon or Pierre Ferrand Cognac.

See Related: Things to Do in Boston, Massachusetts

7. Norman Rockwell Museum

Address: 9 Glendale Rd, Stockbridge, MA 01262

The Norman Rockwell Museum is a short drive from Pittsfield in Stockbridge, Massachusetts. It’s worth the trip to see the most extensive collection of Rockwell’s work from five decades of illustration for The Saturday Evening Post. His art has popular appeal because it reflected American culture throughout the years.

According to Rockwell, his Stockbridge studio, initially located in his backyard on South Street, was his “best studio yet.” Before he died, he left the studio and its contents to the Museum. In 1986, the building was moved to the Norman Rockwell Museum’s grounds.

The 36-acre site features beautiful gardens, stunning views, specimen trees, and sculptures by Rockwell’s son. Visitors can walk through the nature trails, pick apples from the orchard, or head to the Housatonic River.

Many museumgoers purchase food from the onsite cafe and have a picnic, while others use their art materials to sketch on the grounds. Plan at least an hour and a half to tour Norman Rockwell’s studio and galleries; however, many visitors spend extra time on the Museum’s beautiful grounds.

If you plan on seeing Rockwell’s studio, making advanced reservations is a good idea, as it has limited availability. If you want the full experience, reserve a guided tour! Your tour guide will inspire interactive discussion as you walk through the museum.

See Related: Most Beautiful Places in the United Kingdom

8. Springside Park

Address: 874 North St, Pittsfield, MA 01201

Springside Park is a fantastic place to visit if you’re looking for a place to let your little ones burn off some energy. Originally fertile farmland early in the city’s development, Springside Park is now the largest municipal park in Pittsfield. The park includes over 230 acres along the north side of town.

Visitors to the park can hike on one of the many woodland trails, play basketball, climb on one of two playscapes, or explore the pond. There is also the Hebert Arboretum, a living tree museum with over 50 species of native trees, 135 species of wildflowers, and over 300 species of plants.

During the spring and fall, migrating songbirds come for sanctuary and rest. In the southwest section of the park is the Springside House, which dates back to 1856.

The house is the former home of the Pittsfield Parks and Recreation Department and is an integral part of Pittsfield’s past and future. In 2008, the park was listed on the National Register of Historic Places.

See Related: List of US National Monuments

9. Canoe Meadows Wildlife Sanctuary

Address: 309 Holmes Rd, Pittsfield, MA 01201

Canoe Meadows Wildlife Sanctuary is conveniently located just one mile from the center of Pittsfield. The sanctuary attracts wildlife like ospreys, warblers, otters, turtles, and the occasional bear.

Visitors to Canoe Meadows can enjoy several trails that wind through the wetlands, fields, and scenic woods. These nature trails are also along the edge of the scenic Housatonic River.

Birdwatchers can attend one of the weekly guided bird walks in the spring and fall. With more than 60 acres of open fields, the wildlife sanctuary is a breeding habitat for grassland birds. Some birdwatchers have seen White-throated Sparrows, Ruby-crowned Kinglets, Northern Cardinals, Hairy Woodpeckers, Rock Pigeons, and Ring-necked Pheasants.

In addition to nature trails and birdwatching, the sanctuary has a community garden, which rents plots to Mass Audubon members. They also offer accessible raised-bed gardens for those who may need them. Canoe Meadows is a must-do attraction for nature lovers, with access to the scenic woods and wetlands of Berkshire County.

10. Lake Onota

Address: 401-487 Lakeway Dr, Pittsfield, MA 01201

Owned and managed by the city of Pittsfield, Lake Onota is a recreational lake for use by residents and tourists visiting the Berkshires. The 617-acre lake has over 7 miles of shoreline and is roughly a mile wide at its widest point.

Visitors to the lake can fish, boat, kayak, swim, or canoe. Lake Onota is a great swimming hole and is also excellent for fishing, with diverse species like largemouth bass, rainbow trout, bluegill, chain pickerel, and northern pike.

On the eastern shore of Lake Onota is Burbank Park, with a free public boat launch and fishing pier. The 153-acre park is perfect for accessing the lake, with a public swimming beach and a walking path around Lake Onota.

You can rent a boat, canoe, pedal boat, or kayak through Onota Boat Livery. The livery is also a fantastic place to get fishing bait and tackle. And if you’re a rower visiting the area, visit Berkshire Community Rowing to check out their club.

They can set you up in a team boat, or you can rent a single and head out on the lake yourself. If you’re looking for fantastic views and a serene experience, you can’t go wrong with visiting Lake Onata.

If you want to enjoy the morning sounds of the birds while drinking your coffee, stay at a tranquil house conveniently located on the lake! This relaxing five-bedroom home has two small docks and a small beach, with two canoes, five kayaks, and a stand-up paddleboard.

11. Bousquet Mountain

Address: 101 Dan Fox Dr., Pittsfield, MA 01201

Bousquet Mountain is the oldest existing ski area in the Berkshires, opening in 1932. Before becoming a ski area, the mountain was a mink farm owned by Clarence Bousquet. When the Depression hit and the mink farm tanked, Bousquet met with the Mount Greylock Ski Club to cut a 750-foot ski slope to the northern summit of Mahanna Cobble.

Today, Bousquet Mountain is a winter wonderland with 23 ski and snowboard trails, snow tubing, a summit elevation of 1,818 feet, a vertical drop of 750 feet, two chair lifts, two magic carpets, and a terrain park. The recently renovated ski lodge has windows with endless mountain views, a ski rental area, and a restaurant.

However, winter isn’t the only time for recreation at the mountain. Summertime allows for beautiful hikes, including the Mahanna Cobble, a 3-mile out-and-back trail. There are stunning views at the vista, with bird’s eye views of Pittsfield and the North Berkshires.

If you’re looking for a more intense hike, you can take the Yokun Ridge Trail and connecting trails, which comprise more than 10 miles along the Yokun Ridge. Bousquet Mountain is the northern trailhead via the Mahanna Cobble Trail for this hike.

If you visit during the summer, plan on attending one of the mountain’s summer concerts. The family-friendly concerts include blues, jazz, rock, and folk artists.

Regardless of what season you visit, you can plan to wine and dine at one of the two restaurants on the mountain, Lift Bistropub and the Kitchen. If you’re looking for one of Pittsfield’s fun places, look no further than Bousquet Mountain! It’s the perfect ski resort for families, couples, or groups, with year-round dining, recreation, and fun in one place.

See Related: The Ultimate Ski Trip Packing List

Best Places to Stay in Pittsfield

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