15 Best Things to Do in Pittsfield (MA)

The commercial and cultural nucleus for the Berkshires of Western Massachusetts, Pittsfield is an upland city with vistas framed by the Taconic Range to the west and the Berkshire Hills in the east.

Pittsfield had a booming economy at the turn of the 20th century, driven by a forerunner to General Electric.

Along the stately North Street and South Street, the prosperity of that time is obvious, with tall commercial blocks, churches, palatial civic buildings, opulent theaters and a local museum with rich collections.

Since 2005, Pittsfield has been home to the award-winning Barrington Stage Company, renowned for new work like The 25th Annual Putnam County Spelling Bee, which picked up a number of Tony’s in 2004.

1. Herman Melville’s Arrowhead

Author Herman Melville’s (1819-1891) most productive years were spent at this house in the south of Pittsfield.

During his time at Arrowhead from 1850 to 1863, Melville finished Moby-Dick (1851), and wrote Pierre (1852) and The Confidence-Man (1857), before selling up to his brother and moving with his family to New York City.

The house dates back to the 1780s and got its name from Melville because of the arrowheads he would dig 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 returned the interiors to Melville’s time.

You can come to Arrowhead from mid-May to mid-October for tours, and there’s rich programming including live performance, readings, artist talks and guided trail walks.

2. Hancock Shaker Village

On 750 acres in the southwest of Pittsfield is a preserved Shaker commune that was active from the late 18th century to 1960.

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 heritage-breed domestic animals.

There are 20 marvelous historic buildings in situ, such as the rare Round Stone Barn, built in 1826, and designed with an ingenious series of four interior rings.

Throughout the village there are upwards of 20,000 artifacts, including beautifully crafted furniture, while interpreters and skilled artisans give a riveting insight into Shaker life.

Summer brings a wealth of events, from workshops to goat yoga, concerts and the annual Summer Gala in early August.

3. Berkshire Museum

Looking like a Roman villa on South Street, the Berkshire Museum was founded by the newspaperman Zenas Crane, opening in 1903.

In the style of museums from that time, this attraction is a multifaceted cabinet of curiosity, zipping from fine art to engineering, natural history, zoology and ancient civilization.

There are more than 40,000 objects from a multitude of fields in the museum’s collections, and one recent addition is the Feigenbaum Hall of Innovation, a contemporary interactive exhibit exploring the past, present and future of bright ideas.

The permanent exhibition, Objects and Their Stories features rotating selections from the museum’s large reserves, like ancient Egyptian mummies, or plaster casts of iconic works of sculpture such as the Winged Nike of Samothrace.

4. Downtown Pittsfield (Upstreet Cultural District)

Mostly along the broad boulevards, North Street and South Street, Downtown Pittsfield has a real sense of scale for a city of 44,000.

Magnificent turn-of-the-century commercial blocks stand six storys or more, accompanied by civic buildings, courthouses, churches, the Berkshire Museum, a masonic temple and splendid entertainment venues like the Colonial Theatre (1903).

Park Square, the go-to site for protests, is home to the city’s Civil War memorial, erected in 1872. A good first stop is the city’s visitor center at 121 South St, where you can grab an armful of brochures for the area.

One should be the Pittsfield Walking Tour, leading you to 60 plaques for historic sites and buildings along South Street, North Street and Park Place, with a version that can be downloaded online.

5. Barrington Stage Company (BSC)

Since 2005, Pittsfield has been the permanent home for this critically acclaimed regional theatre company. When we wrote this article, the Barrington Stage Company had produced almost 40 pieces of new work.

Many of these had transferred to stages in New York, including the Tony Award-winning musical comedy, The 25th Annual Putnam County Spelling Bee (2004).

The company has several properties around downtown Pittsfield, with a 520-seat Mainstage Theatre (30 Union St) at a venue built for vaudeville in 1912.

There are also shows at the St. Germain Stage, in the Sydelle and Lee Blatt Performing Arts Center (36 Linden St).

When we made this list, the season featured two world premieres, as well as productions of Anna in the Tropics, Waiting for Godot and A Little Night Music.

6. Bousquet Mountain

This highly-rated ski area first opened in 1932, and is the oldest still operating in the Berkshires.

You can get to Bousquet Mountain in under ten minutes from downtown Pittsfield, whether you want to ski, snowboard or simply hit the snow tubing hill.

For this family-friendly activity there are eight lanes with 100% snowmaking coverage and a carpet lift to whisk you back to the top in seconds.

Elsewhere the mountain offers 24 runs on 200 skiable acres, with night skiing and the Yokun Terrain Park. In the summer this spot becomes part of a hiking area along the Yokun Ridge, and hosts a series of outdoor concerts.

7. Lake Onota

Set within city limits there’s a 617-acre lake on Pittsfield’s western shoulder, bordered by woods and 19th-century residences.

Lake Onota is one of the best places to take in the majesty of the Taconic Mountains, which look even prettier as the sun goes down.

In the summer you can head to the Onota Boat Livery to rent a lineup of vessels, from motorized fishing boats to canoes, kayaks, pedal boats and rowboats.

Lake Onota is the setting for Pittfield’s Live on the Lake concert series, with performances every Wednesday evening throughout July and August.

8. Colonial Theatre

Among the magnificent landmarks fronting South Street is this Gilded Age theater that opened in 1903.

Some of the many feted performers to appear at the Colonial Theatre in those early days are Sarah Bernhardt, Douglas Fairbanks Sr, George M. Cohan and Eubie Blake.

For the entire second half of the 20th century the building was used as an art supply store, while holding onto its period decor and fittings.

Praised for its acoustics and preserved turn-of-the-century details, the venue was named a National Historic Treasure in 2000, and underwent a $22 million refurbishment that was completed in 2006.

The Colonial Theatre is managed by the Berkshire Theatre Group, staging musicals, drama and concerts for all tastes

9. Pittsfield State Forest

On Pittsfield’s west flank is an immense state forest over some 11,000 acres of upland scenery. There are woods for miles, with streams, waterfalls and scenic bodies of water like Berry Pond.

This is at the top of Berry Mountain, and with an elevation of 2,150 feet it’s the highest natural body of water in Massachusetts.

In the northeast corner of Pittsfield State Forest you’ll happen upon Balance Rock, a limestone boulder, 15 feet by 30 feet, resting on a tiny base.

There are more than 30 miles of trails for hiking, mountain biking and horseback riding, as well as scores of campsites.

One adventure for more rugged hikers is the Taconic Crest Trail, winding along the NY border atop the ridge of the Taconic Range for 37 miles.

10. Ashuwillticook Rail Trail

When we wrote this article, the 13-mile Ashuwillticook Rail Trail had just been extended into Pittsfield. You can pick up this route at the southern trailhead near the intersection of Crane Ave and Dalton Ave.

Much of the path is on the route of the old Pittsfield and North Adams Railroad, completed in 1846 and eventually abandoned in 1990.

The trail has been opened in several phases since 2001, making its way through Adams, Cheshire, Lanesborough and now a portion of Pittsfield.

Some of the landscapes on the route are exhilarating, especially along the shore of the Cheshire Reservoir, and further north beside the Hoosic River, with the Taconic Mountains on the horizon to the west.

11. Beacon Cinema

An entertainment amenity for a revitalized downtown, the Beacon Cinema is a six-screen multiplex in an historic commercial building.

As you might tell from the facade, the building was a S.S. Kresge 5 & 10 cent store, built in 1918 with intricate terra cotta details on the frieze and upper story.

A downtown movie theater had been a long-term goal for Pittsfield, and the Beacon Cinema opened in 2009.

You can catch first run movies, big-screen classics and even live Met opera presentations, at screens with stadium seating and comfy, heated recliners. This is also one of those rare movie theaters serving alcoholic beverages.

12. Springside Park

Pittsfield’s largest municipal park is on the National Register of Historic Places, and was laid out on a former farm in the early 20th century.

One structure that was already here is the Springside House, a mid-19th century Italianate mansion, with Late Victorian additions.

Found in the southwestern section, this building was previously the parks and rec department’s HQ, and hosts outdoor events on the lawn in summer.

Springside Park is known for its winding wooded trails, which were undergoing a rehabilitation process at the time of writing.

Ongoing work around the park also included the restoration of Springside House, and the restoration of Springside Pond.

13. The Common

On the east side of downtown Pittsfield is a central space for recreation and outdoor events. The Common has a stately feel thanks to the grand Beaux-Arts frontage of the Old Central High School to the east.

There’s a pavilion for summer performances, as well as a large splash pad, a sculpture lawn, picnic area, basketball court and playground.

On Saturday mornings, May through October, the Common is also the location for the Pittsfield Farmers’ Market.

This is officially the first teen-run farmers’ market in the region, for seasonal and local fruit and vegetables, along with fresh roasted coffee, baked goods, honey, meat, eggs, flowers, cheese and more.

Every week you can catch live music, chef demonstrations, workshops and activities for kids.

14. Canoe Meadows Wildlife Sanctuary

Less than a mile from downtown Pittsfield there’s 264 acres of woods, meadows and wetlands on the bank of the Housatonic River.

Canoe Meadows is criss-crossed by three miles of easy, flat trails, with two loops to choose from.

Depending on the time of year, you might come across, or spot signs of, wild species like river otters, beavers, wild turkeys and even an occasional black bear, as well as bird species like osprey, bobolink and great blue heron.

15. Pittsfield Fourth of July Parade

The city has long been known for its impressive 4th of July Parade, which has a history that can be traced back to 1801.

One early documented parade in 1824 featured Revolutionary War veterans and political figures in horse-drawn carriages.

Organized by an independent non-profit group, the parade continues to grow by the year, making its way north through downtown along South Street and North Street.

On a typical year there are more than 1,000 marchers from 175 organizations, with special guest stars, several marching bands, drum corps, dance teams, almost two dozen floats and enormous helium balloons overhead.