Right In The Heart Of Massachusetts' Berkshires Is A Buzzing Artsy City With World-Class Food And Fun

Mention the Berkshires and the mind floods with images of the Boston Symphony Orchestra at Tanglewood. Or a tangle of rivers, lakes, forests, and mountains in the Berkshires — one of New England's most iconic destinations — a paradise for birdwatching, kayaking, and cross-country skiing. At the heart of this enchanting mix of sophistication and serenity is Pittsfield, Massachusetts. This vibrant city in the central Berkshires has a buzzing arts community, world-class gastronomy, and entertainment — both natural and man-made.

Initially inhabited by the Mohican peoples, European settlers later turned the area's 24,000 acres into an agricultural center. The brooks feeding into the Housatonic River helped its early farmers and mills, then Merino wool became its chief export. The town, once home to war heroes and famous figures like "Moby Dick" author Herman Melville, has since transformed its post-industrial identity, focusing on arts, culture, food, and entertainment. Today, Pittsfield could easily be described as the Berkshires' cultural heart.

Pittsfield's lively, ever-evolving Upstreet Cultural District should be the first stop on your visit. Art lovers of all kinds will have their appetites satisfied by its offerings. The Barrington Stage Company's high-quality productions will please theater buffs. The Berkshire Museum's diverse collection of art, history, and science will keep both kids and adults busy for hours. Check out a live gig at Pittsfields' Colonial Theater, a time capsule from the turn of the century. 

All that artsy zigging and zagging could leave you a bit hungry. Good thing Pittsfield has more than a few outstanding restaurants to curb your cravings. Have a hankering for some comfort food? Check out any of the city's six classic diners for a calorie-packed meal. Fancy something a little fancier? Check out Dorothy's Estaminet for an intentionally shabby-chic eatery with elevated classics, sharing platters, even a brunch menu. It also has a full bar, outdoor seating, and live music several evenings per week. 

Fueled up, it's time for some fun. The more adventurous types can head over to the Pittsfield State Forest, a massive Eden in the heart of the Berkshires. Whether by foot, bike, or horseback, it's 30 miles of trails that cover everything from mountains to ponds. Even overnight stays are doable if you bring a tent. There is no wrong time to visit; winter visitors can enjoy cross-country skiing and snowmobiling.

For those traveling from the northeast U.S., Pittsfield is relatively easy to get to on I-90, Highway 20, and Highway 7. There's also seasonal rail service from New York City via Amtrak's Berkshire Flyer. Those flying in from farther afield will likely land at Albany International Airport located 45 miles northwest of Pittsfield. Be sure to grab a rental car as the Berkshires, in general, cover a lot of ground. Plus, a scenic road trip is the best way to capture the best of New England charm.

As for accommodations, expect to spend around $100 and $250 per night, depending on your preferred level of comfort. If you want audacious levels of serenity, there's a quiet romantic retreat nestled in New England's rolling hills in the town of Lenox just 15 minutes away. Pittsfield, however, is for those a bit more down to Earth. Locals enjoy being active, so consider joining their ranks. Campgrounds like the ones in Pittsfield State Forest can be as soothing as they are fun, as long as you're well equipped with seasonally-appropriate gear and clothing.