If you’ll be in Pittsfield this summer, then you should watch out for these fun things to do in Pittsfield.
The commercial and cultural heart of the Berkshires in western Massachusetts, Pittsfield is a highland town with views framed by the Taconic Range to the west and the Berkshire Hills to the east.
Pittsfield had a thriving economy at the turn of the 20th century, driven by General Electric’s predecessor.
Found in the heart of the Berkshires, the city of Pittsfield, Massachusetts, sits majestically in the Berkshire plains.
With its walkable high street lined with red, white, and blue flags and dotted with the work of local craftsmen, it’s a charming mix of old and new, fitting for a region that has experienced a rebirth as a regional travel destination.
Its location is convenient for visitors from the major metropolitan areas of Boston and New York and manages to balance a certain small-town appeal with arts, culture, recreation, and a burgeoning foodie scene to attract a variety of visitors.
Whether you’re headed for a simple walk in the hills outside the city or want top-notch theatre without the big-city prices, Pittsfield has something for you.
Along the stately streets of North Street and South Street, the era’s prosperity is evident, with high-rise commercial blocks, churches, palatial civic buildings, lavish theatres, and a museum having rich collections.
Since 2005, Pittsfield has housed the award-winning Barrington Stage Company, known for new productions such as The 25th Putnam County Spelling Bee, which took home a string of Tonys in 2004.
Keep reading to find out the fun and best things to do in Pittsfield. We’ll urge you to get used to these places as all the fun you’ll have in Pittsfield will come from these places.
Fun Things to Do in Pittsfield
1. Pittsfield Fourth of July Parade
The city is known for its impressive and remarkable 4th of July parade, which can be traced back to 1801.
One of its parades in 1824 featured Revolutionary War veterans and political figures in beautiful, horse-drawn carriages.
The parade was organized by an independent non-profit group and has grown each year, making its way north through downtown along South Street and North Street.
The parade features over 1,000 marchers from 175 organizations with special guest stars, several marching bands, drum corps, dance teams, nearly two dozen floats, and giant helium balloons overhead.
2. Canoe Meadows Wildlife Sanctuary
Less than a mile from downtown Pittsfield is 264 acres of woods, meadows, and wetlands on the banks of the Housatonic River.
Canoe Meadows is crisscrossed by three miles of easy, flat trails with two loops to choose from.
Depending on the time of year, you may encounter or see signs of wildlife such as river otters, beavers, wild turkeys, and the occasional black bear, as well as bird species such as barn owls, bobolinks, and blue herons.
3. Pittsfield Skate Park & Clapp Park
The 2-acre skatepark underwent a complete renovation in 2020 with the help of Rampage Skatepark Equipment. Today, it welcomes brave visitors to test its ramps, rails, and obstacles.
Clapp Park, a year-round playground, is home to a climbing frame, athletic fields, and a whimsical playground.
Come winter, its rolling hills are a popular sledging destination, drawing kids from miles around to race in the fresh powder.
Things to Do in Pittsfield at Night
1. Barrington Stage Company (BSC)
Since 2005, Pittsfield has been the permanent home of this critically acclaimed regional theatre company.
As of this writing, the Barrington Stage Company has produced nearly 40 pieces of new work.
Many of these have been transferred to the New York stage, including the Tony Award-winning musical comedy The 25th Annual Putnam County Spelling Bee (2004).
The company has several properties around downtown Pittsfield, with the 520-seat Mainstage Theater (30 Union St) on a site built for vaudeville in 1912.
There are also performances at St. Germain Stage and at the Sydelle and Lee Blatt Performing Arts Center (36 Linden St).
When we made this list, the season included two world premieres, as well as productions of Anna in the Tropics, Waiting for Godot, and A Little Night Music.
2. Colonial Theatre
Among the grand landmarks fronting South Street is this Gilded Age theatre, which opened in 1903.
Some of the many celebrated artists who appeared at the Colonial Theater in those early days are Sarah Bernhardt, Douglas Fairbanks Sr, George M. Cohan, and Eubie Blake.
Throughout the second half of the 20th century, the building was used as a warehouse for art supplies, retaining its period decoration and furnishings.
Praised for its acoustics and preserved turn-of-the-century details, the site was named a National Historic Treasure in 2000 and underwent a $22 million renovation that was completed in 2006.
The Colonial Theater is managed by the Berkshire Theater Group, which presents musicals, dramas, and concerts for all tastes.
3. Beacon Cinema
Beacon Cinema, an entertainment facility for a revitalized downtown, is a six-screen multiplex in a historic commercial building.
As you could tell from the facade, the building was the S.S. store. Kresge 5 and 10 cents, built-in 1918 with intricate terracotta detailing on the frieze and upper floor.
A downtown movie theatre has been a longtime goal for Pittsfield; the Beacon Cinema opened in 2009.
Catch first-run movies, big-screen classics, and even a live performance of the Met Opera at screens with stadium seating and comfortable heated recliners.
This is also one of those rare cinemas that serve alcoholic beverages.
Things to Do in Pittsfield For Couples
1. Pittsfield State Forest
On the western flank of Pittsfield is a huge state forest of about 11,000 acres of mountain scenery.
For miles, there are forests with streams, waterfalls, and scenic bodies of water like Berry Pond.
Pittsfield state forest is atop Berry Mountain, and 2,150 feet above sea level is Massachusetts’s highest natural body of water.
In the northeast corner of Pittsfield State Forest, you’ll find yourself at Balance Rock, a 15-foot by 30-foot limestone boulder resting on a small base.
There are more than 30 miles of trails for hiking, mountain biking, and horseback riding, as well as dozens of campsites.
One adventure for the more rugged hiker is the Taconic Crest Trail, winding its way along the NY border atop the Taconic Range for 37 miles.
2. Ashuwillticook Rail Trail
As we wrote this article, the 13-mile Ashuwillticook Rail Trail had just been extended to Pittsfield.
You and your other half can pick up this route at the trail’s southern end near Crane Ave and Dalton Ave intersection.
Much of the route is on the old Pittsfield and North Adams Railroad, completed in 1846 and finally abandoned in 1990.
The trail has been open in phases since 2001, making its way through Adams, Cheshire, Lanesborough, and now part of Pittsfield.
Some of the scenery along the route is exciting, especially along the shores of Cheshire Reservoir and further north by the Hoosic River, with the Taconic Mountains on the horizon to the west.
3. Springside Park
Pittsfield’s largest city park is on the National Register of Historic Places and was established on a former farm in the early 1900s.
One structure that has been here before is Springside House, a mid-19th-century Italianate mansion with late Victorian additions.
Located in the southwest section, this building was formerly the Department of Parks and Regeneration headquarters and hosts outdoor events on the lawn during the summer.
Springside Park is known for its winding wooded trails, which were undergoing rehabilitation at the time of writing.
Ongoing work around the park also included the restoration of Springside House and the restoration of Springside Pond.
Things to Do in Pittsfield For Kids
1. Bousquet Mountain
First opened in 1932, this highly-rated ski area is the oldest still operating in the Berkshires.
Whether you want to ski, snowboard, or simply hit the snow tubing hill, Bousquet Mountain is less than ten minutes from downtown Pittsfield.
There are eight lanes with 100% snowmaking for this family activity and a carpet lift that will transport you back to the top in seconds.
Elsewhere, the mountain offers 24 runs on 200 acres of skiing, with night skiing and the Yokun Terrain Park.
This place has become part of the tourist area along Yokum Ridge and hosts many outdoor concerts in the summer.
2. Herman Melville’s Arrowhead
Whether you’re a Moby Dick fan or not, a visit to the historic Melville Mansion is worth adding to your Pittsfield itinerary.
In the author’s 1850-63 home, enjoy a guided tour courtesy of the Berkshire County Historical Society.
The Berkshire county Historical society manages the property. Here, let yourself gaze out the writer’s study window at Mount Greylock, whose perpetual shroud of mist is said to have inspired the larger-than-life whale at the center of the story.
While you’re there, check out the wandering nature trails.
If you have self-publishing or artistic ambitions, explore The Mastheads, which provides studio space for creatives who want to work with the same inspiring background.
3. Berkshire Museum
Art, science, and history come alive at this multi-faceted museum in the heart of Pittsfield.
Housed in a century-old building, you’ll see everything from dinosaur artifacts to exotic fish and a rotating array of exhibits that display the museum’s extensive collection.
Little ones can enjoy targeted family programs like WeeMuse for ages 5 and under, while older kids can contribute to Chow Time at the aquarium.
No matter your age, no visit is complete without a visit to Wally.
Indoor Activities to Do in Pittsfield
1. A Sleep Over at Herman Melville’s Arrowhead
Author Herman Melville (1819–1891) spent his most productive years in this south Pittsfield home.
During his tenure at Arrowhead from 1850 to 1863, Melville completed Moby-Dick (1851) and wrote Pierre (1852) and The Confidence-Man (1857) before selling them to his brother and moving the family to New York.
The house dates from the 1780s and, according to Melville, got its name from the arrowheads he dug up each year during the planting season.
Members of the Melville family owned the property until 1927, and in 1975 it was purchased by the Berkshire County Historical Society, which restored the interiors to Melville’s time.
You can come to Arrowhead from mid-May to mid-October for tours, and there is an extensive program including live performances, readings, artist talks, and guided trail walks.
2. Hancock Shaker Village
On 750 acres in southwest Pittsfield is a preserved Shaker commune that was active from the late 18th century until the 1960s.
Now a living history museum, the village is still part of a working farm, the oldest in the Berkshires, with extensive fruit and vegetable gardens and livestock.
There are 20 magnificent historic buildings on site, such as the rare round stone barn, built in 1826 and designed with an ingenious series of four inner rings.
There are more than 20,000 artifacts throughout the village, including beautifully crafted furniture, while interpreters and skilled artisans provide a fascinating insight into Shaker life.
Summer brings a plethora of events, from workshops to goat yoga, concerts, and the annual Summer Gala in early August.
3. Berkshire Museum
The Berkshire Museum, which looks like a Roman villa on South Street, was founded by journalist Zenas Crane and opened in 1903.
In the style of museums of the time, this attraction is a multifaceted cabinet of curiosities, from fine arts to engineering, natural history, zoology, and ancient civilization.
There are more than 40,000 objects from many fields in the museum’s collections. One recent addition is the Feigenbaum Hall of Innovation, a contemporary interactive exhibit exploring bright ideas’ past, present, and future.
The permanent exhibition Objects and Their Stories features rotating selections from the museum’s large holdings, such as ancient Egyptian mummies or plaster casts of iconic statues such as the Winged Nike of Samothrace.
Romantic Things to Do in Pittsfield
1. Downtown Pittsfield (Upstreet Cultural District)
Downtown Pittsfield, mostly along the wide boulevards, North Street and South Street, has a real sense of scale for a city of 44,000.
Magnificent turn-of-the-century commercial blocks are six stories or more, accompanied by civic buildings, courthouses, churches, the Berkshire Museum, the Masonic Temple, and great entertainment venues such as the Colonial Theater (1903).
Park Square, a popular spot for protests, is home to the city’s Civil War Memorial, which was built in 1872.
A good first stop is the city’s visitor center at 121 South St, where you can pick up an armful of brochures about the area.
One should be the Pittsfield Walking Tour, which takes you to 60 plaques of historic sites and buildings along South Street, North Street, and Park Place, with an online downloadable version.
2. Lake Onota
Within the city limits, on the west arm of Pittsfield, is a 617-acre lake bordered by woods and 19th-century residences.
Lake Onota is one of the best places to enjoy the majesty of the Taconic Mountains, which look even more beautiful when the sun goes down.
In the summer, you can head to Onota Boat Livery and rent a range of craft, from motorized fishing boats to canoes, kayaks, paddle boats, and rowboats.
Lake Onota is the venue for Pittsfield’s Live on the Lake concert series, which takes place every Wednesday evening during July and August.
3. Common
On the east side of downtown Pittsfield are a central area for recreation and outdoor events.
The Common has a majestic feel due to the magnificent Beaux-Arts facade of Old Central High School to the east.
There is a pavilion for summer performances, a large mat, a sculpture lawn, a picnic area, a basketball court, and a playground.
On Saturday mornings, May through October, the Common is also the site for the Pittsfield Farmers Market.
This is officially the region’s first youth farmers market featuring seasonal and local fruits and vegetables, along with freshly roasted coffee, baked goods, honey, meat, eggs, flowers, cheese, and more.
You can watch live music, cooking demonstrations, workshops, and activities for children weekly.
Cheap Things to Do in Pittsfield
1. Facsimile Outlet Store, Springside Park, and Bousquet Ski Area
Eclectic gifts are the name of the game at this curated shop in the heart of Pittsfield. You can find it between The Square and the Berkshire Museum.
This 246-acre park on Pittsfield’s north side is home to hiking trails, baseball and softball fields, a pair of playgrounds, and plenty of nature and history.
The hotel’s Springside House is on the National Register of Historic Places, and the Vincent J. Herbert Arboretum offers peaceful relaxation.
Bousquet Mountain has long been a local favorite, and recent improvements have made it a year-round destination for visitors.
Pittsfield Locals have flocked to this ski resort for generations, and the addition of a brand-new ski lodge ensures its future.
In the off-season, find hiking, concerts, and other entertainment in the mountains.
2. First Friday Art Walk
Put on your walking shoes on the first Friday of the month as downtown Pittsfield hosts a block-long art festival where local businesses display works by local artists, who are often on hand to greet visitors during the show’s debut.
If you miss this month-long celebration, take note: Most of the art is on display throughout the month, so you can enjoy it at your leisure—just download the Downtown Pittsfield app to access the map.
As if that weren’t enough, art is seemingly everywhere on the streets of Pittsfield, from the Welcome to Pittsfield mural that greets visitors at the train station to the uniquely painted utility boxes located throughout the city and the Ruby Bridges mural on Center Street.
3. Berkshire General Store
With all the charm of a country store, Berkshire General is home to Boar’s Head Deli and plenty of snacks, plus a fun and entertaining selection of toys and gifts.
Its giant picture windows on North Street will catch the attention of pint-sized passers-by!
Free Things to Do in Pittsfield
1. Pittsfield Halloween Parade and The Boulders
Although it hasn’t been held since before the pandemic, keep an eye on plans for the Pittsfield Halloween Parade, where the city is going all out — and has been for more than 70 years — to celebrate the spooky season.
Explore The Boulders Nature Reserve for a beautiful, easy hike with the kids.
Explore more than six miles of hiking trails in this preserve managed by the Berkshire Natural Resources Board, including wetlands, waterfalls, towering hemlock forests, and stunning vistas.
2. Beacon Cinema in Pittsfield and Canoe Meadows Wildlife Sanctuary
Located in the middle of the main drag, the Beacon Cinema looks like an old cinema – with ticket prices to match – but has some new-age perks like reserved seating and heated recliners.
Bird and wildlife watchers flock to this preserve just one mile from downtown to explore the beautiful trails that wind along the scenic Housatonic River.
Watch everything from otters to owls, warblers, turtles, and even bears – sir!
3. Pittsfield Suns Baseball
Summer means college baseball in New England, and the Pittsfield Suns will take up residence in more than 100-year-old Wahconah Park from late June through early August.
More than 200 Suns players have played in the MLB. The wooden grandstand is one of the last remaining in the US and seats only 4,500, so you’re guaranteed an intimate experience.
Cool Places to Visit in Pittsfield
1. District Kitchen & Bar
Farm-to-table food is served in an airy, picturesque space just off the main drag. A well-stocked bar and impressive wine list make it an easy sell to parents, while the decadent macaroni and bread pizza satisfied the kids in our crew.
2. King Horse and Hot Dog Ranch
Located across the street from The Common, King Kone may not look like much early in the morning, but by evening, the line for these sumptuously served delicacies stretches for blocks.
While there’s a full menu to choose from, don’t go to the Hot Dog Ranch without ordering its Famous Baby Hot Dogs.
The traditional order is served with mustard, onion, and gravy, although other options include relish, sauerkraut, ketchup, and cheese.
But take note: There has long been debate in this town about whose dogs reign supreme: Hot Dog Ranch or…
3. Berkshire Theater Group & Barrington Stage Company
With three separate theatres under its ownership, Berkshire Theater Group produces a wide variety of shows throughout the year.
Pittsfield’s Colonial Theater combines Gilded Age architecture with a state-of-the-art technology system to make it a world-class venue, whether the Berkshire Theater hosts in-house or imported musicians, comedians, and traveling acts.
Barrington Stage Company’s high-quality productions and commitment to new work have won rave reviews far beyond Pittsfield.
The regional theatre company’s first national success came with the premiere of the 25th annual Putnam County Spelling Bee in 2004, which transferred to Broadway, won a pair of Tony Awards, and is currently developing as a Disney film.
Its 2022 season includes eight separate productions on two stages, including a youth production of The Supadupa Kid.
Want to get even closer to the stage? Join a series of FREE lobby chats with artists and producers throughout the season.
Conclusion
Pittsfield is not your usual vacation city, yet, you’ll be itching for another time here after the first vacation.
Have fun doing all the best fun things to do in Pittsfield.
