Discover the Best Berkshire Towns: Where New England Charms Unfold

Lenox isn't just a cultural haven—it's the cool kid of the Berkshires. Tanglewood Music Center, the summer hotspot for the Boston Symphony Orchestra, sets the tone for an eclectic blend of musical vibes. Dive into the side streets, where historic mansions like The Mount share real estate with indie boutiques and eateries offering inventive farm-to-table fare. In Lenox, culture doesn't just mean symphonies—dig a little deeper and you’ll see that it means curated experiences and a vibe that's effortlessly cool. But don’t worry, you’ll fit right in.

Once an industrial powerhouse, North Adams has reinvented itself with a gritty charm that's hard to ignore. MASS MoCA, housed in an old mill complex, is more than an art museum, it’s also a canvas of contemporary expression. But, the town's revival isn't limited to art—take a hike up Mount Greylock, and you'll find an outdoorsy side that's as authentic as it gets. North Adams is where industrial grit meets artistic grace, creating an unexpected blend that you’ll enjoy experiencing every step of the way.

Stockbridge is a living embodiment of New England charm. While you can stroll down Main Street, it's the offbeat corners and hidden gems that reveal Stockbridge's true character. From the Berkshire Botanical Garden to the tranquil Ice Glen trail, Stockbridge invites you to discover its layers beyond the iconic images. This town isn't frozen in time, it’s tastefully slow-paced and just waiting to be explored.

The town of Lee might be small, but it packs a punch of surprises. The historic downtown is a vibrant mix of old-world charm featuring modern boutiques and culinary gems. Beyond the town's limits, October Mountain State Forest is a playground for outdoor enthusiasts. Stay in Lee to experience a unique small town with a big personality.

Pittsfield, the largest city in the Berkshires, balances an urban spirit with an outdoorsy feel. The Colonial Theatre serves as a dynamic stage for Broadway vibes and indie performances. Artscape—a volunteer-led committee that sponsors, plans, and oversees an annual juried exhibition of public art—transforms outdoor spaces and enhances the overall character of downtown. Pittsfield State Forest encompasses not just trails and lakes but offers an urban escape seamlessly integrating arts, culture, and the great outdoors.

New England Inns and Resorts was founded in 1907 and has been devoted to providing unforgettable experiences ever since. With over 300 hotels, inns, and resorts located across New England, we support exceptional hospitality with a dedication to keeping it local at every location. 

In the Berkshires, every town has its own unique story. Whether you're drawn to Lenox's effortless cool, North Adams' industrial chic, Stockbridge's living canvas, Lee's small-town surprises, or Pittsfield's urban-nature fusion, the Berkshires promise an offbeat getaway that defies expectations. So come along for the ride and experience a stay you’ll never forget at New England Inns and Resorts.