23 Best & Fun Things to Do in Pittsfield (MA)

Pittsfield city is located in Berkshire County in Massachusetts, United States, lying on the Housatonic River headstreams. It is the county’s seat.

It is the largest city in Berkshire County. Pittsfield was estimated to have a population of forty-three thousand nine hundred and twenty-seven during the 2020 census.

Pittsfield was named in honor of William Pitt, an English prime minister. It was incorporated in 1891 as a city.

Visit Pittsfield and explore the dynamics of the city ranging from its dramatic outdoor spaces to its artistic community and adventure experience.

The city features a good number of attractions, such as the Berkshire Museum, Hancock Shaker Village, Canoe Meadows Wildlife Sanctuary, Wandering Star Craft Brewery, Bousquet Mountain, and more.

If you’re planning a trip to Pittsfield, here are the top things to do in Pittsfield, MA.

Things to Do in Pittsfield, MA

1. Pittsfield State Forest

Are you a nature lover? This place is definitely for you! Pittsfield State Forest Is an excellent outdoor destination for outdoor enthusiasts.

Pittsfield State Forest is an 11,000-acre property featuring waterfalls, upland scenery, woodland, streams, and more.

You should also check out Berry Pond. It is located at the peak of Berry Mountain, which has a height of 2,150 feet. The Pond is recognized as Massachusetts’ tallest natural water body.

The Balance Rock is at the northeastern end of Pittsfield State Forest, a unique limestone boulder lying on a small spot.

Pittsfield State Forest features over 30 miles of open trails for horseback riding, mountain biking, hiking, and camping.

You also get to enjoy the relaxing sound of overflowing streams and the nice songs of the birds in the region.

This State Forest is one of the best places to visit in Pittsfield, MA. Visit it with your travel companions and explore all the natural resources here.

Address: 1041 Cascade St, Pittsfield, MA 01201, United States

2. Lake Onota

If you have been searching for a perfect escape from the crowds, visit Lake Onota. It is one of the best places to visit in Pittsfield, MA.

Lake Onota is a perfect place to get away from the buzz and noise of the city. It encompasses six hundred and seventeen acres.

The Lake offers visitors a countless number of outdoor recreational activities which are water-related and perfect for all ages.

You can rent a kayak, paddleboard, or canoe and explore the calm and shimmering waters or go fishing in search of fresh catch.

Visitors can also dive into the waters as a perfect way to cool off on a hot day or have an excellent picnic time with their significant other.

Make sure you don’t miss the series of concerts on the Lake, including Wednesday’s live performances from July to August.

Address: Lake Onota, Pittsfield, Massachusetts 01201, United States

3. Downtown Pittsfield

You haven’t visited a city if you don’t explore its Downtown region, so make sure you add an exploration of Downtown Pittsfield to your checklist of the top things to do in Pittsfield, MA.

Downtown Pittsfield is packed with an assortment of businesses and organizations that caters to the needs of all visitors.

Stop by some of the stores, which are filled with a wide variety of items to beautify the home, including souvenirs.

The region offers a wide variety of dining options through the immense number of restaurants available and functioning.

You will find beautiful historic buildings, including churches, civic buildings, a Masonic Temple, courthouses, the Berkshire museum, and more.

To solidify your experience, join the Pittsfield Walking Tour, which takes you through several historic buildings and sites.

Address: 33 Dunham Mall UNIT 102, Pittsfield, MA 01201, United States

4. Hancock Shaker Village

If you’re embarking on an educational trip, exploring Hancock Shaker Village is one of the best things to do in Pittsfield, MA.

Hancock Shaker Village is worth spending a day or more as it spreads for seven hundred and fifty gorgeous acres.

The Village is home to Berkshire’s oldest working farm, which would blow your mind through the Shaker community’s inventive, architectural, and engineering features.

You will find a large collection of household items and shaker exhibits on display in the twenty original ancient buildings of the Village.

Hancock Shaker Village offers you an opportunity to explore the shaker community’s gardens and farms, including heritage livestock, herbs gardens, and more.

The unique Round Stone Barn, constructed in 1826 in Hancock Shaker Village, is a venue for several events during summer, including concerts, yoga, workshops, and more.

Address: 1843 W Housatonic St, Pittsfield, MA 01201, United States

5. Bousquet Mountain

What could be better than having a fantastic experience in a winter wonderland? Possibly nothing!

Do hesitate to include enjoying winter-based games in Bousquet Mountain to your list of fun things to do in Pittsfield, MA, with your pals.

Bousquet Mountain is a true gem of the winter season, which has existed since 1932 and has become a vital part of the community.

You’re offered different activities, such as snowboarding, skiing, and snow tubing, including joining their snowsports programs and lessons.

It consists of a 750 ski slope which is available for both beginners and professionals as they are ready to offer guidance.

Bousquet Mountain is home to a 9-hole golf course with wading pools featuring six water slides and a zipline available during summer.

Address: 101 Dan Fox Dr, Pittsfield, MA 01201, United States

6. Berkshire Museum

If you want an eye-opening adventure, add a visit to Berkshire Museum to your list of what to do in Pittsfield, MA.

Berkshire Museum is an attraction that offers visitors an exciting educational opportunity, as it is open for tours.

The Museum showcases an extensive collection of historical artifacts, fine arts, and natural science samples, offering an eye-opening experience.

You will be captivated by the hands-on exhibits through which you discover the region’s rich history and natural sciences.

Berkshire Museum was established in 1903 by Zenas Crane, a newspaperman focusing on different sectors, including old civilization and zoology.

There are permanent exhibitions and objects as well as their stories, including temporary selections such as historical Egyptian mummies or iconic sculptures.

Address: 39 South St, Pittsfield, MA 01201, United States

7. Beacon Cinema

Suppose you have been searching for a place where you can comfortably enjoy an intriguing movie in the city. In that case, check out the Beacon Cinema.

The Beacon Cinema was established in 2009. It has gradually become a favorite place for many families due to its level of consistency.

The Cinema provides comfortable stadium seating with contemporary reclining seats, which offers great relaxation once you push a button.

It is fully equipped with the latest sound technology with an immense concentration on the frequency and phase of the sound system.

The Beacon Cinema offers visitors a variety of blockbuster movies on large screens, including live shows of Met Opera and classics.

It is one of the few movie cinemas that offer alcoholic drinks, including delicious popcorn and other non-alcoholic drinks.

Address: 57 North St, Pittsfield, MA 01201, United States

8. Canoe Meadows Wildlife Sanctuary

Canoe Meadows Wildlife Sanctuary is a tranquil location for a quiet walk as you immerse in its beautiful natural environment.

Well-paved walking trails wind down through the gorgeous fields, woods, wetlands, and marshes, and they’re open for hiking.

Depending on the time of the year, you also get to meet several kinds of wildlife, including turtles, warblers, otters, ospreys, bears, and more.

Address: 309 Holmes Rd, Pittsfield, MA 01201, United States

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9. Colonial Theatre

Among the best things to do in Pittsfield, MA is a visit to Colonial Theatre. This place celebrates the community’s artistic side.

Colonial Theatre is famous for its incredible historical architectural design, which goes back to 1903 when it was established.

As a historic theater, it is encompassed by striking details of the majestic area with a seating of seven hundred and twenty people.

This place is a haven for talented artists and theatre zealots with numerous kinds of shows, including comedies and musicals.

The Colonial Theatre is operated by the Berkshire Theatre Group, organizing dramas and concerts for everyone to enjoy.

Many artists have graced the stage of Colonial Theatre, such as Eubie Blake, Douglas Fairbanks Sr, Sarah Bernhardt, and George M. Cohen.

Address: 111 South St, Pittsfield, MA 01201, United States

10. The Home of Herman Melville at Arrowhead

The Home of Herman Melville at Arrowhead is fixed along Holmes Road as a beautiful yellow house dating back to the 18th century.

Stunning lush greeneries surround the building as it was previously the home of Herman Melville, a prominent American author.

He produced his literary pieces here from 1850 to 1963; Herman published Confidence-Man, Moby-Dick, and Pierre.

You’re allowed to explore the Home of Herman Melville at Arrowhead and get a closer view of the life lived by Herman.

Herman spent a huge part of his life at the Home of Herman Melville at Arrowhead; there is no better place to learn about him than his home.

The Melville family later owned the Home of Herman Melville at Arrowhead before it was sold to Berkshire County Historical Society in 1975.

This establishment is also the center for various activities, including artist talks, readings, live performances, docent-led trail walks, and tours from the middle of May to October.

Address: 780 Holmes Rd, Pittsfield, MA 01201, United States

11. The Berkshire Hills Country Club

One perfect way to spend your day in Pittsfield is by swinging your club in one of the most beautiful golf courses in the city. It is one of the fun things to do in Pittsfield, MA.

The Berkshire Hills Country Club is described as a center with nicely manicured fairways, pristine green, and water hazards with varying elevations.

The golf course is somewhat challenging but perfect for both beginners and professional golf players, offering them the excitement they need.

This particular attraction was established in 1925 and is the only golf course designed by A.W. Tillinghast in Massachusetts.

You can stop by the clubhouse for refreshing drinks and snacks before or after your tee time.

Berkshire Hills Country Club is an excellent choice for a wedding and other intimate events due to its romantic setting and gorgeous views of the facility.

There is a golf store that is fully packed with a wide variety of golfing instruments and attire for both men and women.

Address: 500 Benedict Rd, Pittsfield, MA 01201, United States

12. Guido’s Fresh Marketplace

Guido’s Fresh Marketplace is a family-owned and operated market in Pittsfield that has served the people since 1983.

It originally began in 1979, when two brothers, Matt and Chris Masiero, came together to develop the original Guido’s through their experience in retail and culinary arts.

They grew quickly and had to open Guido’s Fresh Marketplace in search of a bigger setting in 1983 with numerous dealers.

Guido’s Fresh Marketplace offers the freshest farm produce, ranging from flowers and fish to meats and locally prepared dishes.

The theory of Guido’s Fresh Marketplace offers vendors a chance to operate their businesses independently, providing an extensive collection dedicated to quality.

At Guido’s Fresh Marketplace, you can purchase beers and wines, kitchen tools, gift items, customized items, and more.

Address: 1020 South St, Pittsfield, MA 01201, United States

13. The Barrington Stage Company

Another great attraction in Pittsfield, the Barrington Stage Company, is a place every local or visitor should visit for amazing live entertainment.

The Barrington Stage Company offers live performances presented by gifted artists as an award-winning theatre.

This theatre is a venue for high-quality dramas, musicals, comedies, great classics, and many other fresh performances.

You can support the community’s art scene when you reserve seats for a show for you and your family and friends.

Barrington Stage Company was founded in 2005 and has continuously served the community up until this day as a prominent local theatre.

The theatre can accommodate up to five hundred and twenty persons presenting world-class productions, including A Little Night, the Tropics, and more.

Address: 30 Union St, Pittsfield, MA 01201, United States

14. Pontoosuc Lake

If you’re in the mood for casting lines and patiently waiting for a fresh catch, Pontoosuc Lake is the best place for you.

Pontoosuc Lake is a scenic attraction in the boundaries between Lanesborough and Pittsfield towns with its dribbling waters.

You can cast your fishing lines into the waters and catch different species of fish. The Lake is also open for paddling as another perfect way to explore the soothing waters and gorgeous views of the area.

Pontoosuc Lake is an excellent escape to the quietest parts of the city, away from the noisy and busy areas.

Address: 10 Hancock Road, Pittsfield, MA 01201. United States

15. The Common

The Common is a public area for outdoor events and recreational activities. It is located in the downtown area of Pittsfield.

This area offers an authentic grand vibe due to the Old Central High School’s elegant Beaux Art orientation on the east side.

 It consists of a pavilion used for summer concerts, a gigantic splash pad, and a playground that keeps children engaged.

The Common comprises a basketball court, a sculpture lawn, and a picnic area for those who would like to have a nice picnic.

It is the venue for the Pittsfield Farmers’ Market, which offers a wide variety of farm produce, including eggs, baked goods, cheese, honey, flower, meat, and more.

Try as much as possible to catch some live music performances, workshops, chef presentations, and kids’ activities held weekly.

Address: 100 1st St, Pittsfield, MA 01201, United States

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16. Whitney Center for the Arts

Whitney Center for the Arts is housed in Thomas Colt House, an 1865 historic building and the former home of the club of the Berkshires women.

This creating and displaying art center has two standard art galleries offering performances like concerts, Dramas, comedies, opera nights, and musicals.

The art center hosts children and teens events providing a private performance platform that is available for rentals.

Whitney Center for the Arts was founded in 2012 by Lisa Whitney, a native of Pittsfield, which she named after her parents.

Address: 42 Wendell Ave, Pittsfield, MA 01201, United States.

17. The Pittsfield Farmers Market

Of course, visit the Pittsfield Farmers Market whenever you want to go shopping for any item in Pittsfield.

Pittsfield Farmers Market officially opened in 2013 as the region’s first market to be operated by teens. It is open throughout the year.

This seasonal market is open from May to October from 9 am to 1 pm on Saturdays. From November to April, it is open once a month.

They have successfully created an accessible market that enlightens the public about the benefits of nutrition, offering food programs.

The Pittsfield Farmers Market offers workshops, chef demonstrations, activities for children, live music, and more.

Also, get the opportunity to meet and interact with many locals and get to learn more about their culture and how their native means are made.

Address: 100 1st St, Pittsfield, MA 01201, United States

18. The Springside Park

The Springside Park is the largest municipal Park in Pittsfield. It is listed on the National Register of Historic Places.

This Park was founded on what was formerly a farm way back in the 20th century. It is home to a 19th-century Springside House, an Italianate mansion.

You will find the former parks and rec department headquarters in the southwest corner of the building, with a lawn where outdoor events are held.

Springside Park is popular for its trails winding through the wood areas, which are also adequately maintained.

The Park features a community garden, the Hebert Arboretum, a pond, a basketball court, softball and baseball fields, and two playgrounds.

Address: 874 North St, Pittsfield, MA 01201, United States

19. Fontaine’s Auction Gallery

Fontaine’s Auction Gallery has been in business for more than five years. It is a must-visit for anyone who wants unique accessories.

Fontaine’s Auction Gallery has always come through for many sellers and buyers in the world through selling and purchasing jewelry, antiques, fine art, and more.

Their experts have a wide knowledge of the International background and market situations working hand in hand with consignors and collectors.

They have continued to be at the top of their game when it has to do with great quality, a high level of honesty, and professionalism.

Fontaine’s Auction Gallery offers you unique items from anywhere in the world in perfect condition and rates.

Address: 1485 W Housatonic St, Pittsfield, MA 01201, United States

20. Circa

Circa is located in the Downtown region of Pittsfield, elegantly designed with authentic high tin ceilings and old hardwood floors.

You will find a free large parking space and street parking at the side of the building. Circa also offers delivery of any item for an extra fee.

They offer modern lighting and furniture, including vintage clothing, local art, estate, and Berkshire gift items made in the city.

Circa offers high-quality collectibles, home decor, antique items, and more from Mid-century, adding more color to your space.

If you want to add more elegance and luxury to your personal space, stop by this store and purchase the highest quality items.

Their staff is down to earth, and they’re known for offering the best services ensuring that their customers are satisfied at the end of the day.

Address: 436 North St, Pittsfield, MA 01201, United States

21. Pittsfield Fourth of July Parade

Typically, Pittsfield is known for its rich and undying history, and the amazing Fourth of July Parade is one event for which it is also known.

The Pittsfield Fourth of July Parade has been a constant practice in the city since 1801. It is a highly anticipated event.

In 1824, the Parade spotlighted political figures and revolutionary war vets on carriages drawn by horses. An independently operated non-profit organization organizes this Parade.

The event has continuously grown and expanded annually, extending through the city’s downtown district.

The Pittsfield Fourth of July Parade features drum corps, special guest shows, numerous floats, over one thousand marchers, and more.

Suppose you genuinely want to integrate into the community through its cultures and traditions. In that case, this is a must-add to your itinerary.

Address: Pittsfield, MA 01201, United States

22. Wandering Star Craft Brewery

Are you a beer lover? Then, visiting Wandering Star Craft Brewery ought to be on your list of what to do in Pittsfield.

Wandering Star Craft Brewery is a 15-barrel brewery in the city which produces draft beers distributed throughout the area.

The company has continuously distributed a wide variety of well-refined brews in cans and kegs across Berkshire County.

They offer drinks like American Blonde Ale, Losing My Edge ESB, lobby juice, mild at heart, red nose eye, Raindrop Pale Ale, Wobbly Pop New England IPA, thunderbolt IPA, Horatio Single Hop IPA, and more.

The Brewery is always open on Saturdays, while tours, off-site sales, and tastings are available on special holidays.

Wandering Star Craft Brewery is a host to a good number of private and public events held throughout the year.

Address: 11 Gifford St, Pittsfield, MA 01201, United States

23. Bloom Brothers

Bloom Brothers was established by Berkshire County’s three brothers offering various sorts of lab-certified cannabis items.

Licensed manufacturers and cultivators make these products. It is open to adults twenty-one years and above.

They are concerned with making the visitors’ experience an amazing experience through their exceptional services.

Bloom Brothers feature an experienced team ready to answer every question and help you find the perfect product.

Address: 2 Larch St, Pittsfield, MA 01201, United States

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Plan Your Trip to Pittsfield

Inarguably, Pittsfield proclaims itself as one of the cities you will visit.

After going through the list above, you will definitely understand why Pittsfield attracts thousands of tourists annually.

Pittsfield is perfect for the entire family as there are numerous things to do for the young and old.