15 Best Things to Do in Pittsfield (MA)

Pittsfield, located in the heart of Berkshire County in Western Massachusetts, is a charming city with a population of over 42,000 people. It serves as the largest city in the county and acts as the hub for both cultural and economic activity.

The city is surrounded by picturesque mountains and boasts a rich history, natural beauty, and a lively community.

Pittsfield has a thriving and diverse economy, including healthcare, education, tourism, and technology. Berkshire Medical Center, the region’s largest healthcare provider, is located in the city, along with several public and private schools, including Berkshire Community College. Pittsfield boasts numerous cultural attractions, such as the Berkshire Museum, the Colonial Theatre, and the Barrington Stage Company, which produces award-winning theater productions.

The city is surrounded by the Berkshire Mountains, which offer a plethora of year-round activities such as hiking, skiing, and other outdoor pursuits. Several parks and recreational areas, including the Pittsfield State Forest and the Onota Lake Recreation Area, provide ample opportunities to enjoy the great outdoors.

In this article, we’ve curated a list of the 15 best things to do in Pittsfield, so you can make the most of your visit to this enchanting city. Whether you’re a fan of scenic hikes, historic landmarks, or lively cultural events, Pittsfield has something to offer everyone. 

So, without further ado, let’s explore the top activities and attractions that make Pittsfield such an exciting destination to visit.

1. Pittsfield State Forest

Source: flickr.com

Nestled in the heart of Pittsfield, Massachusetts, lies the magnificent Pittsfield State Forest, spanning over 11,000 acres. This lush forest offers visitors an escape from the hustle and bustle of city life and a chance to explore nature’s beauty at its finest.

Hiking is one of the most popular activities in the Pittsfield State Forest, attracting visitors from far and wide. With its varied terrain, from rugged landscapes to dense woodlands, the forest offers over 30 miles of trails that cater to all levels of hikers, making it an excellent spot for adventure seekers.

Camping in the Pittsfield State Forest is a memorable experience. Visitors can set up camp in one of the multiple campsites available, surrounded by nature’s serenity. With breathtaking views of the forest and its tranquil surroundings, camping in the Pittsfield State Forest is an ideal way to escape into nature.

The Pittsfield State Forest is also a favorite spot for mountain biking and biking enthusiasts. The forest features miles of trails that weave through the woods, offering mountain bikers and cyclists an exhilarating off-road experience. The panoramic views of the forest from the bike trails are a sight to behold.

For water enthusiasts, canoeing, kayaking, swimming, and non-motorized boating are popular activities in the forest’s two picturesque ponds, Berry Pond and Balance Rock Pond. Anglers can also cast their lines and enjoy fishing in the tranquil ponds.

Hunting and horseback riding are permitted in designated areas of the forest, adding a touch of adventure to the visitors’ experience.

Visitors to the Pittsfield State Forest can also participate in educational programs and guided tours. Off-road vehicle enthusiasts can enjoy exploring the forest on designated trails, and in winter, cross-country skiing and snowmobiling are popular activities.

The Pittsfield State Forest is an ideal spot for anyone seeking a natural escape, with its vast woodlands, scenic trails, serene ponds, and educational programs. This breathtaking forest offers something for everyone, making it a must-visit destination for nature lovers and outdoor enthusiasts alike.

2. Hancock Shaker Village

Source: flickr.com

Hancock Shaker Village is truly a gem among the many historical sites that dot the landscape of the United States. Once home to a thriving Shaker community, the village is now a living history museum that allows visitors to experience the way of life of this unique religious group.

As you step onto the grounds of Hancock Shaker Village, you are immediately transported back in time. The village features a number of beautifully preserved buildings, each with its own story to tell. From the Round Stone Barn, which was once home to a bustling dairy operation, to the elegant Shaker Dwelling House, which housed the community’s leaders, each building is a testament to the Shakers’ commitment to excellence and innovation.

One of the most impressive aspects of Hancock Shaker Village is the Shakers’ dedication to simplicity and self-sufficiency. The community was known for its exceptional craftsmanship, and visitors can see this for themselves in the many examples of Shaker furniture and textiles on display. The village also features a number of gardens and fields, which were carefully tended by the Shakers and provided much of the community’s food.

Source: flickr.com

But perhaps the most striking aspect of Hancock Shaker Village is the sense of peace and tranquility that permeates the grounds. As you wander through the gardens or sit in the shade of a tree, it’s easy to forget the hustle and bustle of modern life and imagine what it must have been like to live in this serene and contemplative community.

Whether you’re a history buff, an architecture enthusiast, or simply someone looking for a break from the stresses of daily life, Hancock Shaker Village is a must-see destination. So why not plan a visit and experience the unique charm and beauty of this historic site for yourself?

3. Herman Melville’s Arrowhead

Source: flickr.com

Arrowhead is a historic home that was once the residence of Herman Melville, one of America’s most prominent authors. From 1850 to 1863, Melville lived and wrote some of his most famous works at Arrowhead, including “Moby-Dick,” “Pierre,” and “The Confidence-Man.” Today, Arrowhead remains a popular destination for literary enthusiasts and history buffs alike, who come to experience the home where Melville spent his formative years as a writer.

When Melville first arrived in Pittsfield, he rented Arrowhead, a farmhouse originally built in the 1780s, from a local farmer. In 1856, Melville purchased the 160-acre farm and found inspiration for many of his literary works here.

Today, Arrowhead has been beautifully preserved, and visitors can take a tour of the house and see Melville’s writing desk where he penned many of his famous works. The house has been restored to its mid-19th century appearance, complete with period furnishings and décor, offering visitors a glimpse into the life of the Melville family during their time at Arrowhead.

One of the most intriguing aspects of Arrowhead is the stunning view from the house. From Melville’s study, he had a clear view of Mount Greylock, the highest peak in Massachusetts. This mountain is said to have inspired the mountain in “Moby-Dick.” Visitors can also stroll through the farm, which has been preserved as a working farm, with a variety of animals and crops.

In addition to its literary significance, Arrowhead has played a vital role in local history. During the 19th century, the farm was a hub of activity, with the Melvilles hosting gatherings and parties for their friends and neighbors. Today, Arrowhead hosts an array of events and programs throughout the year, including literary readings and historical reenactments.

Overall, Arrowhead is a must-see destination for anyone interested in American literature or history. The home is a beautiful tribute to the life and work of one of America’s most celebrated authors, and it provides a captivating glimpse into the history of the region. Whether you are a fan of Melville’s work or just curious about exploring the rich cultural heritage of New England, Arrowhead is an excellent choice for an enriching and enjoyable visit.

4. Berkshire Museum

Source: flickr.com

The Berkshire Museum in Pittsfield, Massachusetts is a one-of-a-kind museum that offers an exciting opportunity for visitors to discover a diverse range of art, science, and history exhibits. With a rich history dating back to its founding in 1903, the museum’s impressive collection is sure to capture the attention of people of all ages and interests.

The museum is divided into several sections, each with its unique focus. The art section showcases an extensive range of paintings, sculptures, and other art forms from local and international artists.

Visitors can explore works from the Hudson River School, a group of American landscape painters from the mid-19th century, as well as contemporary art exhibits that feature the talents of modern artists.

Source: commons.wikimedia.org

The science and history section of the museum is equally impressive, featuring exhibits that cover a broad range of topics such as natural history, geology, astronomy, and technology. The museum’s dinosaur exhibit is a particular highlight, showcasing the fossils of prehistoric creatures that once roamed the Earth.

The museum also offers interactive exhibits that provide visitors with hands-on learning experiences such as the “Living Laboratory” exhibit that explores the ecology of the Berkshires.

One of the most unique exhibits at the museum is the “Curiosity Incubator,” which inspires visitors to explore their creativity and curiosity. This exhibit offers a variety of hands-on activities and workshops that allow visitors to experiment with different materials and techniques, from 3D printing to fiber arts.

Source: flickr.com

In addition to its permanent collection, the Berkshire Museum also hosts a variety of temporary exhibits throughout the year. These exhibits cover a wide range of topics and interests, from photography and sculpture to history and science.

In my opinion, the Berkshire Museum is a fantastic destination for anyone interested in exploring the arts, sciences, and history of the Berkshires. With its diverse collection, engaging exhibits, and unique programs and workshops, it is an attraction that should not be missed by visitors to Pittsfield and beyond.

5. Bousquet Mountain

Source: pexels.com

Bousquet Mountain is a breathtaking ski resort located in Pittsfield, Massachusetts that offers incredible scenery, exciting slopes, and exceptional skiing and snowboarding facilities. Whether you’re a beginner or an advanced skier, you’re sure to find a slope that suits your skills and preferences. With its variety of slopes, terrain parks, and black diamond runs, Bousquet Mountain is a must-visit destination for anyone who loves skiing or snowboarding.

But Bousquet Mountain isn’t just for winter sports enthusiasts. During the summer months, the mountain transforms into a lush green oasis that’s perfect for hiking and mountain biking. Visitors can also cool off at the water park or explore the region’s charming towns, museums, and art galleries.

One of the things that make Bousquet Mountain truly special is its rich history. The resort has been welcoming visitors for over 80 years, and it has played a significant role in the development of skiing and snowboarding. The mountain has hosted many events and competitions, and it has served as a training ground for professional skiers and snowboarders.

Moreover, Bousquet Mountain is located in the heart of the Berkshires, a region known for its stunning natural beauty and cultural attractions. Visitors can take advantage of the area’s picturesque state parks, charming towns, and cultural offerings.

Bousquet Mountain is a fantastic destination for anyone who loves the outdoors, skiing, and snowboarding. With its picturesque location, challenging terrain, and rich history, the resort offers an unforgettable experience that visitors are sure to cherish for years to come.

6. Downtown Pittsfield

Source: commons.wikimedia.org

Welcome to Downtown Pittsfield, a charming and historic area in Massachusetts that draws visitors from all around the world. Even though the city is home to just 44,000 people, it has a unique feel to it, thanks to the magnificent turn-of-the-century buildings, churches, courthouses, and entertainment venues.

The heart of Downtown Pittsfield is North Street and South Street, two boulevards lined with beautiful buildings dating back to the early 1900s. These buildings have been preserved and restored, giving us a glimpse into the city’s rich history and unique architecture.

If you’re looking for entertainment, Downtown Pittsfield has a lot to offer. You can visit the Berkshire Museum, the masonic temple, or the Colonial Theatre, which was built in 1903 and is a must-visit for theater enthusiasts. The theater has a beautiful interior and hosts a variety of shows throughout the year.

Park Square is another popular spot in Downtown Pittsfield. It’s located right in the heart of the city and is a gathering place for protests and rallies. The Civil War memorial, which was built in 1872, is also located in the square, adding to the area’s historical significance.

If you’re interested in learning more about the history of Downtown Pittsfield, make sure to visit the visitor center at 121 South St. You can pick up brochures and maps of the area, including the Pittsfield Walking Tour, which takes you to 60 different historic sites and buildings along South Street, North Street, and Park Place. If you’re feeling tech-savvy, you can also download the walking tour online.

Downtown Pittsfield is also a hub of arts and culture. The Upstreet Cultural District, which encompasses the heart of Downtown Pittsfield, is home to numerous galleries, studios, and performance spaces. The district hosts events and festivals throughout the year, including the annual 10×10 Upstreet Arts Festival, which celebrates the arts in all their forms.

Downtown Pittsfield is a charming and historic area that offers visitors a unique look into the city’s rich history and culture. Whether you’re interested in architecture, entertainment, history, or the arts, there’s something for everyone in Downtown Pittsfield.

7. Barrington Stage Company (BSC)

Source: pexels.com

Barrington Stage Company (BSC) is a really cool theater in Pittsfield, Massachusetts that puts on all kinds of plays and musicals. It was started back in 1995 by a woman named Julianne Boyd, and since then it’s become a pretty big deal in the theater world.

The people at BSC are all about telling stories in new and exciting ways. They like to mix things up and try new stuff, which is probably why they’ve won so many awards over the years, including a bunch of Tony Awards.

Their main theater, the Boyd-Quinson Mainstage, is a really beautiful space with over 500 seats. It’s right in the middle of downtown Pittsfield, which makes it a really important part of the community.

But BSC isn’t just about big shows in a big theater. They also have a smaller, more intimate theater called the St. Germain Stage, where they put on new plays and musicals and sometimes even cabaret performances. And they work with local schools through their Playwright Mentoring Project to help students learn how to write plays.

One of the coolest things about BSC is that they’re always looking for new and exciting stories to tell. They have an annual Musical Theatre Lab where writers, composers, and actors come together to create new musicals. Some of these shows have even gone on to be produced at other theaters around the country.

BSC is also really committed to making sure that everyone feels welcome and included. They’re always working to make sure that people from all different backgrounds and experiences are represented on their stages, and that everyone who comes to see a show feels comfortable and at home.

In my viewpoint, Barrington Stage Company is a really important part of the Pittsfield community and the theater world in general. They’re always pushing the boundaries and trying new things, and they’re committed to making sure that everyone feels welcome and included.

8. Lake Onota

Source: flickr.com

Nestled in the picturesque city of Pittsfield, Massachusetts, Lake Onota is a breathtaking body of water that spans over an impressive 617 acres. It’s no surprise that this tranquil lake is a popular spot for both locals and visitors, who can’t resist its serene waters and stunning scenery.

One of the unique features that sets Lake Onota apart is its division into north and south basins, which are separated by an old roadway. The lack of water exchange between the two basins has resulted in each developing its own distinct ecosystem and characteristics. The city of Pittsfield takes great pride in preserving the lake’s natural beauty for future generations to enjoy.

Lake Onota has a rich history that dates back to the late 19th and early 20th centuries when wealthy vacationers built grand summer homes along its shores. These mansions now stand as a testament to the lake’s storied past and the significant role it played in the lives of the region’s elite.

Source: flickr.com

Lake Onota is a haven for outdoor enthusiasts. Fishing aficionados will be thrilled to hear that the lake is home to an array of fish species, including largemouth bass, smallmouth bass, chain pickerel, and yellow perch. Swimmers can take a dip in the crystal-clear waters, while water skiers and jet skiers can enjoy the lake’s smooth surface.

Sailing is a popular activity on Lake Onota, with the Williams Ephs men’s and women’s crews frequently rowing on its waters. The lake is also renowned for its summer concert series, “Live on the Lake,” which showcases local talent and draws large crowds.

Camp Winadu, a beloved summer camp for boys, is situated along the lake’s shores and offers a wide range of outdoor activities, from swimming to boating and fishing.

Source: flickr.com

All in all, Lake Onota is a true gem that caters to all tastes. Whether you’re seeking relaxation or adventure, this beautiful lake in Pittsfield, Massachusetts, is an ideal destination for anyone seeking to connect with nature and enjoy the great outdoors.

9. Colonial Theatre

Source: flickr.com

The Colonial Theatre is an architectural wonder that has captured the hearts of audiences since its construction in 1903. Its stunning turn-of-the-century interior, designed by Joseph McArthur Vance and J.B. McElfatrick, has been well-maintained by its various owners over the years and has hosted some of the biggest names in theater, including George M. Cohan, Sara Bernhardt, and John Barrymore.

Although it was closed in 1951, the theater’s magnificence was protected by George Miller and his son, Steven, who preserved many of its features during its transformation into a Miller’s Art Supply Store. This allowed for the eventual restoration of the theater to its former glory, a process that was documented in photographer Nicholas Whitman’s book, The Colonial Theatre: A Pittsfield Resurrection.

In 1998, First Lady Hillary Clinton designated the Colonial Theatre as a National Historic Treasure. This recognition spurred the community to invest over $22 million in renovating the 100-year-old theater, which is one of the few surviving Vaudeville-era theaters and is renowned as one of the finest acoustical theaters in the world.

After years of restoration work, the Colonial Theatre reopened its doors to the public in 2006. Since then, it has continued to attract top performers from various genres, including James Taylor and the Lovin’ Spoonful. Today, it remains a beloved cultural institution and one of the best attractions in Pittsfield.

Visitors to the Colonial Theatre can enjoy a wide variety of performances, ranging from musical acts to theatrical productions. The theater also hosts special events, such as film screenings and talks by prominent artists and thinkers. Its beautiful interior, complete with ornate decorations and intricate details, provides a stunning backdrop for any performance.

In my judgment, The Colonial Theatre is an iconic cultural institution that has played a significant role in the history of Pittsfield and the wider theater community. Its restoration serves as a testament to the power of community investment and dedication to preserving historic landmarks. Whether you have an affinity for the arts or an appreciation for beautiful architecture, the Colonial Theatre is certainly worth a visit.

10. Ashuwillticook Rail Trail

Source: flickr.com

The Ashuwillticook Rail Trail offers visitors a chance to experience the beauty of the Hoosac River Valley. The trail passes between Mount Greylock and the Hoosac Mountains and is flanked by Cheshire Reservoir, the Hoosic River, and associated wetland communities.

The name “Ashuwillticook” comes from the American Indian name for the south branch of the Hoosic River and means “the pleasant river in between the hills.” The trail is a wonderful way to experience the natural beauty of the region and learn about its history.

Whether you are a serious cyclist or just looking for a leisurely stroll, the Ashuwillticook Rail Trail is the perfect destination. With its beautiful scenery and well-maintained trail, it is a great place to spend a day exploring with family and friends.

Source: flickr.com

So, if you are looking for an outdoor adventure in western Massachusetts, be sure to check out the Ashuwillticook Rail Trail.

11. Beacon Cinema

Source: facebook.com/beaconcinema/

It is one of several locations owned and operated by Phoenix Theatres Entertainment, a Michigan-based movie theater chain.

The Beacon Cinema features state-of-the-art technology including 3D screens and surrounds sound systems. It also offers stadium seating, luxury recliner seats, and a full-service bar and lounge.

The theater shows a mix of blockbuster movies and independent films, and often hosts special events such as film festivals and live broadcasts of theatrical productions.

The Beacon Cinema also has space available for private events such as corporate meetings, birthday parties, and private screenings.

My viewpoint, the Phoenix Theatres Beacon Cinema is a popular destination for moviegoers in the Pittsfield area, offering a high-quality moviegoing experience in a comfortable and modern setting.

12. Springside Park

Source: commons.wikimedia.org

Springside Park is a beautiful and serene public park. The park is spread across 237 acres of lush greenery, and it provides ample opportunities for visitors to engage in outdoor activities and recreational pursuits.

The park’s main entrance is located at the end of Springside Avenue, where visitors are greeted by a welcoming arch. Upon entering the park, visitors are greeted with an array of picnic areas and playgrounds for children. There are also various sports fields and courts, including basketball and tennis courts, as well as a horseshoe pit.

One of the most notable features of Springside Park is the network of hiking trails that weave through the park’s forests, meadows, and hillsides. These trails offer visitors an opportunity to explore the park’s natural beauty and observe the local flora and fauna. The trails are well-maintained and offer varying degrees of difficulty, making them accessible to hikers of all skill levels.

Another highlight of Springside Park is the historic Springside House, which was built in the mid-1800s and is now listed on the National Register of Historic Places. The house is open for tours, and visitors can learn about the history of the park and the local area. The house is also a popular venue for weddings and other special events.

The park is also home to a picturesque pond, which is a popular spot for fishing and boating. In the winter months, the pond freezes over and becomes a prime spot for ice skating.

13. The Common

The Common is a public park located in the heart of downtown Pittsfield. It is a popular spot for locals and visitors alike to gather, relax, and enjoy the outdoors.

The park features a large grassy area with plenty of benches and picnic tables, making it a great spot for a picnic or to enjoy lunch on a nice day. The park also has a playground area for children, as well as a splash pad for hot summer days.

The Common is home to a number of events throughout the year, including outdoor concerts, festivals, and holiday celebrations. The park is also a popular destination for outdoor weddings and other special events.

The Common has a rich history, dating back to the 18th century when it was used as a training ground for the local militia. Today, it remains a beloved gathering place for the community and a symbol of Pittsfield’s rich cultural heritage.

14. Canoe Meadows Wildlife Sanctuary

Source: flickr.com

Canoe Meadows Wildlife Sanctuary is a nature reserve. The sanctuary is open year-round and offers visitors a variety of opportunities to explore the natural world.

One of the main attractions of Canoe Meadows Wildlife Sanctuary is its diverse wildlife. The sanctuary is home to many different species of birds, including woodpeckers, herons, and warblers, as well as mammals such as deer, beavers, and muskrats. Visitors can enjoy birdwatching, hiking, and wildlife viewing throughout the sanctuary’s network of trails.

In addition to its wildlife, Canoe Meadows Wildlife Sanctuary features several wetlands, ponds, and streams that provide important habitats for many species of plants and animals. The sanctuary’s forests, meadows, and fields are also home to a variety of wildflowers and other plant species.

Canoe Meadows Wildlife Sanctuary offers several educational programs and events throughout the year, including guided hikes, birdwatching tours, and nature camps for children. The sanctuary is also available for private events, such as weddings and other special occasions.

Overall, Canoe Meadows Wildlife Sanctuary is a great destination for nature lovers and anyone looking to explore the beauty of the Berkshires region of Massachusetts.

15. Pittsfield Fourth of July Parade

Source: pexels.com

The Pittsfield Fourth of July Parade is an annual event held in Pittsfield, to celebrate the Independence Day of the United States of America. The parade is one of the largest and most popular events in the Berkshires region, drawing thousands of spectators from all over the state.

The parade features a wide range of participants, including marching bands, community groups, floats, and military units. The procession starts at the corner of South Street and West Housatonic Street and proceeds north on South Street, then turns east on Park Square before continuing down North Street to Wahconah Street.

There are also many other events and activities taking place in Pittsfield on the Fourth of July, including live music, food vendors, fireworks, and more. The festivities typically start early in the morning and continue well into the night.

If you’re planning on attending the Pittsfield Fourth of July Parade, be sure to arrive early to find a good spot along the parade route, as it can get quite crowded. You may also want to bring a lawn chair or blanket to sit on, as well as sunscreen and plenty of water, as it can get quite hot in the summertime.

The Pittsfield Fourth of July Parade is a great way to celebrate America’s independence and enjoy the company of friends and family in a festive, community-oriented atmosphere.

15 Best Things to Do in Pittsfield (MA)

  1. Pittsfield State Forest
  2. Hancock Shaker Village
  3. Herman Melville’s Arrowhead
  4. Berkshire Museum
  5. Bousquet Mountain
  6. Downtown Pittsfield (Upstreet Cultural District)
  7. Barrington Stage Company (BSC)
  8. Lake Onota
  9. Colonial Theatre
  10. Ashuwillticook Rail Trail
  11. Beacon Cinema
  12. Springside Park
  13. The Common
  14. Canoe Meadows Wildlife Sanctuary
  15. Pittsfield Fourth of July Parade