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As the largest Berkshires city and official regional county seat, Pittsfield, Massachusetts beckons visitors with an enticing mix of artistry, history and scenery.
The one-time industrial hub, which sits just about equidistant between the northern Berkshires town of North Adams and southern Berkshires town of Great Barrington, provides the perfect home base for travelers looking to explore the entire region.
Before they do, however, any visitor should spend at least a few days in Pittsfield itself and its unique Upstreet Cultural District.
Dedicated in 2012, the district brings together just about all of the elements that make Pittsfield special. Here’s a look at how passersby might spend their time there.
Pittsfield Park Square at holiday time by Patrick Barry
In an area with many excellent art scenes, Pittsfield has one of the most distinguished. The Barrington Stage Company (BSC), located right downtown, attracts 50,000+ guests each year and has a host of awards to its name, including multiple Tony awards. In addition to renditions of classics, the BSC also premieres a number of its own works, including a couple that have made it all the way to Broadway.
The Colonial Theatre is another first-class showplace, where concerts of all types fill up the bill. The theater has welcomed everyone from the Boston Symphony Orchestra to Grateful Dead revival bands into its majestic interior, which was once Gilded Age playhouse. Along with the music, there are family-friendly shows and performances by locals, too, so give the schedule a look before you head into town.
This former Gilded Age playhouse still very much looks the part
In addition to excellent venues, the Upstreet Cultural District is home to several special events throughout the year. Each August, the WordxWord festival takes place, during which visiting poets blend together verse, spoken word and storytelling in a weeklong gathering that’s free to attend.
The 10×10 Upstreet Arts Festival, a recent inclusion to the February happenings in downtown Pittsfield, features something for onlookers of all interests. 10×10 brings together fireworks, theater, art, comedy, magic, dance and more, creating a winter spectacle that’s definitely worth a trip to take in.
On Third Thursdays, which take place from May through October, North Street shuts down and the streets showcase all kinds of entertainment. Musicians play, artists perform, galleries stay open late and there are a variety of activities, including sidewalk dining, after-hours shopping and more.
One such Third Thursday during July in Pittsfield
Beyond arts, Pittsfield also has plenty to pique the interest of travelers with a more historical curiosity. The Berkshire Museum boasts one of western Massachusetts’ finest permanent collections, along with numerous exhibitions and activities for guest of all ages. The museum’s scope spans not just art and history, but also natural science, including some intriguing critters!
Outside Berkshire Museum in Pittsfield during spring
For those willing to venture just a bit south of the cultural district, there’s another historic spot worth seeing, particularly for literature lovers. Herman Melville, the great American author, made his home just a few miles from the museum at Arrowhead, where he penned Moby-Dick and several other works. Tours of the site are available, courtesy of the Berkshire Historical Society.
Arrowhead during summertime by Tim Grafft
Public art is another big part of Pittsfield’s cultural district. In total, there are more than 30 outdoor works, ranging from sculptures to murals to art installations. These adornments make walking the downtown area plenty of fun in and of itself; along the way, there does happen to be a fine array of spots for shopping and eating, too.
While in town, there’s no shortage of places to stay, either. Crown Plaza Pittsfield-Berkshires is just a few steps from the Berkshire Museum’s door, while the Berkshire Inn is only a few blocks farther away. There are a host of other options as well, listed in full here.
A most inviting room at the Crown Plaza Pittsfield-Berkshires
While the Upstreet Cultural District offers more than enough to fill up a trip, families might also consider venturing just a bit outside downtown. Hancock Shaker Village, a spellbinding living history museum located five miles away, is a great outing destination for young ones. During the winter months, Bousquet Ski Area is another top nearby spot for families, who will be most pleased by the reliably reasonable rates.
Snowboarding down Bousquet Mountain by Ogden Gigli
To learn more about how you can make the most of a trip to Pittsfield, click here. For a look at what else there is to do in western Massachusetts, just click here.
Have you ever taken a trip to Pittsfield? What caught your eye around town? Tell us in the comments below!