Top 15 Attractions and Activities in Pittsfield, MA

Pittsfield serves as the commercial and cultural center of the Berkshires in Western Massachusetts. It is an upland city framed by the Taconic Range to the west and the Berkshire Hills to the east.

During the early 20th century, Pittsfield experienced significant economic growth, largely attributed to a precursor of General Electric.

The architectural remnants of that prosperity are evident along North Street and South Street, featuring tall commercial buildings, churches, grand civic structures, luxurious theaters, and a local museum housing extensive collections.

Since 2005, Pittsfield has been the home of the esteemed Barrington Stage Company, celebrated for new productions such as The 25th Annual Putnam County Spelling Bee, which received multiple Tony Awards in 2004.

1. Herman Melville’s Arrowhead

Author Herman Melville (1819-1891) spent his most prolific years in this residence situated in the southern part of Pittsfield.

From 1850 to 1863, while at Arrowhead, Melville completed Moby-Dick (1851), and composed Pierre (1852) and The Confidence-Man (1857), subsequently selling the property to his brother before relocating with his family to New York City.

This historic home dates back to the 1780s, earning its name from the arrowheads frequently unearthed by Melville each year during planting season.

The Melville family maintained ownership of the property until 1927, after which it was acquired in 1975 by the Berkshire County Historical Society, which restored the interiors to reflect Melville’s era.

Arrowhead is open for tours from mid-May to mid-October, offering an array of enriching programming, including live performances, readings, artist discussions, and guided nature walks.

2. Hancock Shaker Village

Situated on 750 acres in the southwestern region of Pittsfield lies a historically preserved Shaker community, operational from the late 18th century until 1960.

Now functioning as a living history museum, this site remains an active farm, recognized as the oldest in the Berkshires, featuring extensive fruit and vegetable gardens along with heritage breed domestic animals.

The village encompasses 20 remarkable historic structures, including the unique Round Stone Barn, constructed in 1826, designed with an innovative series of four interior rings.

With over 20,000 artifacts dispersed throughout the village, expertly crafted furniture is complemented by demonstrations from interpreters and skilled artisans, who provide fascinating insights into Shaker life.

During the summer season, a diverse range of activities includes workshops, goat yoga, concerts, and the annual Summer Gala in early August.

3. Berkshire Museum

The Berkshire Museum, resembling a Roman villa on South Street, was established by newspaperman Zenas Crane and opened its doors in 1903.

This attraction embodies the essence of museums from that era, serving as an eclectic cabinet of curiosity, crossing disciplines such as fine art, engineering, natural history, zoology, and ancient cultures.

Boasting over 40,000 objects from various domains within its collections, the museum recently added the Feigenbaum Hall of Innovation, an interactive exhibit that examines the evolution of innovative ideas through time.

The permanent exhibition titled Objects and Their Stories features rotating selections from the museum’s extensive reserves, showcasing items such as ancient Egyptian mummies, as well as plaster casts of iconic sculptures like the Winged Nike of Samothrace.

4. Downtown Pittsfield (Upstreet Cultural District)

Along the extensive boulevards of North Street and South Street, Downtown Pittsfield presents a tangible sense of scale for its 44,000 residents.

Impressive turn-of-the-century commercial buildings, often reaching six stories or more, accompany civic structures, courthouses, churches, the Berkshire Museum, a Masonic temple, and exquisite performance venues like the Colonial Theatre (1903).

Park Square serves as a prominent site for demonstrations and is home to the city’s Civil War memorial, which was erected in 1872. A visit to the city’s visitor center at 121 South St is highly advisable for collecting informative brochures about the area.

A noteworthy starting point is the Pittsfield Walking Tour, guiding visitors to 60 plaques marking significant historic sites and buildings along South Street, North Street, and Park Place, with an accessible version available online.

5. Barrington Stage Company (BSC)

Since its establishment in 2005, Pittsfield has been the permanent home for this highly regarded regional theatre company. At the time of this writing, the Barrington Stage Company had presented nearly 40 new productions.

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

The company operates several venues in downtown Pittsfield, including a 520-seat Mainstage Theatre (30 Union St) located in a building that originally served as a vaudeville theater in 1912.

Additionally, performances occur at the St. Germain Stage, situated within the Sydelle and Lee Blatt Performing Arts Center (36 Linden St).

During the season of this article, the lineup 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 regarded ski area, which commenced operations in 1932, remains the oldest skiing venue still in service within the Berkshires.

Bousquet Mountain is conveniently located under ten minutes from downtown Pittsfield, offering options for skiing, snowboarding, and an exhilarating snow tubing experience.

The tubing hill features eight lanes with complete snowmaking coverage and a carpet lift, allowing for rapid ascents back to the top.

In addition, the mountain boasts 24 ski runs across 200 acres, night skiing facilities, and the Yokun Terrain Park. In summer, this area transforms into a hiking destination along the Yokun Ridge and hosts a series of outdoor concerts.

7. Lake Onota

Nestled within city limits, Lake Onota spans 617 acres on the western edge of Pittsfield, surrounded by lush woodlands and 19th-century residences.

This picturesque lake is among the premier locations to appreciate the grandeur of the Taconic Mountains, particularly at sunset.

During the summer months, the Onota Boat Livery provides a variety of rental options, including motorized fishing boats, canoes, kayaks, pedal boats, and rowboats.

Lake Onota also serves as the venue for Pittsfield’s Live on the Lake concert series, featuring performances every Wednesday evening throughout July and August.

8. Colonial Theatre

Among the splendid landmarks lining South Street, this Gilded Age theater inaugurated in 1903 stands out prominently.

Notable performers who graced the Colonial Theatre stage during its formative years include Sarah Bernhardt, Douglas Fairbanks Sr., George M. Cohan, and Eubie Blake.

For the latter half of the 20th century, the building was utilized as an art supply store while maintaining its period decor and fixtures.

Renowned for its exceptional acoustics and preserved early 20th-century features, the venue was designated a National Historic Treasure in 2000 and underwent a $22 million restoration completed in 2006.

The Colonial Theatre is operated by the Berkshire Theatre Group, hosting a diverse array of musicals, dramas, and concerts.

9. Pittsfield State Forest

Located on the western edge of Pittsfield, this expansive state forest extends over 11,000 acres of elevated terrain. Visitors can explore vast woodlands, streams, waterfalls, and scenic bodies of water, including Berry Pond.

Berry Pond, at an elevation of 2,150 feet, holds the distinction of being the highest natural body of water in Massachusetts.

In the northeast corner of Pittsfield State Forest, one can explore Balance Rock, a limestone boulder measuring 15 feet by 30 feet, precariously balanced on a small base.

The forest features over 30 miles of trails suitable for hiking, mountain biking, and horseback riding, accompanied by numerous campsites.

The more adventurous hiker may opt for the Taconic Crest Trail, which traces the NY border along the Taconic Range for 37 miles.

10. Ashuwillticook Rail Trail

At the time of this writing, the 13-mile Ashuwillticook Rail Trail had recently been extended to include a segment in Pittsfield, accessible at the southern trailhead near the intersection of Crane Ave and Dalton Ave.

The majority of the trail follows the path of the former Pittsfield and North Adams Railroad, established in 1846 and subsequently abandoned in 1990.

Opened in phases since 2001, the trail now traverses through Adams, Cheshire, Lanesborough, and a portion of Pittsfield.

The scenic landscapes along this route are exhilarating, particularly along the shore of Cheshire Reservoir and further north beside the Hoosic River, with the Taconic Mountains gracing the horizon to the west.

11. Beacon Cinema

The Beacon Cinema stands as a vibrant entertainment venue in a revitalized downtown area, featuring a six-screen multiplex housed within a historic commercial structure.

The building originally operated as a S.S. Kresge 5 & 10 cent store, constructed in 1918, showcasing intricate terra cotta details on its frieze and upper levels.

The long-desired downtown cinema opened its doors in 2009.

Patrons can enjoy first-run films, classic movies, and even live Metropolitan Opera broadcasts in theaters equipped with stadium seating and comfortable, heated recliners. This cinema is notably one of the few to offer alcoholic beverages on-site.

12. Springside Park

Springside Park, the largest municipal park in Pittsfield, is listed on the National Register of Historic Places, established on the grounds of a former farm in the early 20th century.

One notable structure is the Springside House, an Italianate mansion from the mid-19th century featuring Late Victorian additions.

Located in the southwestern part of the park, this building previously served as the headquarters for the parks and recreation department and hosts outdoor events during the summer months.

The park is praised for its meandering wooded trails, which were undergoing rehabilitation at the time of this writing.

Restoration efforts also included Springside House and Springside Pond.

13. The Common

The Common, located on the eastern side of downtown Pittsfield, provides a central space for recreation and outdoor events. This area boasts a dignified atmosphere, enhanced by the grand Beaux-Arts facade of the Old Central High School to the east.

Facilities include a pavilion for summer performances, a sizable splash pad, a sculpture lawn, picnic areas, a basketball court, and a playground.

Every Saturday morning from May through October, The Common serves as the venue for the Pittsfield Farmers’ Market.

This market is notable for being the first teen-run farmers’ market in the region, featuring seasonal and local produce alongside fresh roasted coffee, baked goods, honey, meats, eggs, flowers, cheese, and more.

Each week, attendees can enjoy live music, cooking demonstrations, workshops, and activities designed for children.

14. Canoe Meadows Wildlife Sanctuary

Located less than a mile from downtown Pittsfield, Canoe Meadows Wildlife Sanctuary encompasses 264 acres of woodlands, meadows, and wetlands along the Housatonic River.

This sanctuary is crisscrossed with three miles of easy, flat trails, offering two loops for visitors to select from.

During different seasons, one may encounter various wildlife, including river otters, beavers, wild turkeys, and occasionally a black bear, in addition to numerous bird species such as osprey, bobolink, and great blue heron.

15. Pittsfield Fourth of July Parade

Pittsfield is historically recognized for its extraordinary Fourth of July Parade, with roots tracing back to 1801.

A documented parade from 1824 featured Revolutionary War veterans and notable political figures riding in horse-drawn carriages.

This parade, organized by an independent non-profit organization, continues to expand annually, progressing through downtown along South Street and North Street.

Typically, the event showcases more than 1,000 participants from 175 organizations, including special guest stars, several marching bands, drum corps, dance teams, approximately twenty floats, and large helium balloons floating above.