7 Reasons to Drive to the Berkshires, Massachusetts

Traveling to Massachusetts isn’t all just about Boston, okay? In fact, a trip to the Berkshires practically serves as an antithetical experience to the state’s capital city. Located just around three hours from NYC, the region is a bucolic dream any season with winding, scenic roads, charming properties, and top notch restaurants.

The fun of the Berkshires is that it truly does feel like an escape from all that is NYC, which also made it a go-to destination for some of America's most famous literary figures. The region is especially ideal for outdoor adventures, which is why the fall is one of its most popular travel seasons to indulge in some world class leaf peeping and more.

Regardless of the time of year, at the Berkshires, expect beautiful sights, great food, and some of the best museums in the country. The possibilities are endless, but here are seven of our favorite reasons to make the drive.

First and foremost, it feels important to describe what exactly the Berkshires are. The region is technically referred to as Berkshire County, and is the westernmost county in the state. As a part of the Appalachian range, the whole area is nestled within the Taconic Mountains, the Housatonic River, and the Hudson Highlands. Don’t expect dramatic peaks, though, as the range is much more rolling than rocky.

Like many destinations in New England, the Berkshires are a true reflection of the seasons. During the winter, expect powdery snow and an influx of skiers, while the fall brings a magnificent display of colors. Driving through the region in the spring and summer you’ll see fields of goldenrod and other wildflowers breaking through the green, blooming along the hills.

The Berkshires are, in a way, western Massachusetts’ answer to the Hamptons. There’s no way to sugar coat it: it’s a bougie place to vacation. Though where the two match one another on charm factor and fanciness, they definitely differ in attitude. Aside from the fact that the Berkshires doesn’t have a beach (queue up the classic question that pits beach people against those who prefer the mountains), it’s also much more low key.

A laid back destination, it lends itself nicely to a weekend retreat with a great bottle of scotch and good friends, rather than a boozy night out on the town like one might enjoy in Montauk. It makes sense, considering the area was partly made famous by literary figures escaping their otherwise hectic lives in the city for pastoral splendors. Here, they purchased country estates (called cottages) that look more like castles—many of which are still available to tour around today.

There are tons of ways to experience nature in the region that present a wide range of difficulty, from the well-manicured Berkshires Botanical Garden for pleasant strolling to scaling Mount Greylock for a day-long hike. For those looking for a sweet spot in between the two, hikes to spots like Olivia’s Overlook are perfect. Look out for signage at the beginning to participate in a self-guided mindfulness hike, too, which begins with an audio meditation to ground yourself.

Another local favorite is Bash Bish Falls which can be reached hiking from two different states. Hiking from Massachusetts, you’ll reach the falls in less than a mile, and coming from New York, the journey is around a mile and a half. Either way, reward yourself with the sight of two falls diverging around rocks and coming together in a large pool below. Unfortunately, swimming isn’t allowed but it’s definitely still worthy of a visit.

Natural splendor can also be found at Natural Bridge State Park, where you can view the only white marble arch in North America—carved out from glacial melt over 13,000 years ago.

Fans of farm-to-table dining will be right at home in the Berkshires, where fresh, seasonal produce is pretty much the name of most restaurants’ games. Prairie Whale, opened by Mark Firth of Marlow & Sons in Brooklyn, has a wide open patio with ample lawn seating and calls upon local produce to craft their menu—some even coming from Firth’s own farm. Nudel Restaurant is another local favorite, whose menu shifts daily.

For a more historic and one-of-a-kind experience, the Old Inn on the Green is off the grid and entirely lit by candle. The Red Lion Inn is known by locals as a quintessential Berkshires experience with tons of stories to tell. Grab a seat at their Main Dining Room serving New England classics, or the more rustic (and also family-friendly) Widow Bingham’s Tavern serving burgers, house-made chili, and plenty of pints. For Vietnamese fare, Truc Orient Express has been an area stalwart for more than forty years. Xicohtencatl offers authentic Mexican cuisine; the Italian American menu of Frankies also includes vegan options; and Berkshire Mountain Bakery has breads and best sellers like their oatmeal pecan cookie.

Visitors to the Berkshires have always been inspired by these unique landscapes, even famed author Herman Melville, who loved vacationing there so much he eventually decided to make the move. At one point he was set up on a literary blind date with another author, Nathaniel Hawthorne who wrote “The Scarlet Letter,” and the two hiked up Monument Mountain together near Lenox. Supposedly, during that hike, Hawthorne gave Melville advice on what direction he should take on the book he was working on—a little known novel named “Moby Dick.”

Today, you’re able to end your hike on Monument Mountain and head straight to Melville’s home called Arrowhead. It’s located in the town of Stockbridge, where you can also find the Norman Rockwell Museum. Rockwell gained fame for his paintings and illustrations depicting American life, and his long-time residence is what he once called his “best studio yet.” The museum is home to rotating exhibitions of his work, complete with 570 of his illustrations and much more.

One of the most popular attractions in the area is called The Mount, which was once home to the esteemed author Edith Wharton—the first woman to win the Pulitzer Prize in Literature. Located in the town of Lenox, it’s a huge property that was created as a more practical, American interpretation of European mansions. Here, have lunch at the terrace cafe, explore the rooms of the estate, and wander its gorgeous grounds.

No trip to the Berkshires is complete without checking out one of the largest contemporary art museums in the country, the Massachusetts Museum of Contemporary Art, or MASS MoCA. The massive inventory of works is spread out over 250,000 feet in 19 galleries within a renovated 19th century factory, whose industrial campus was expanded in 2017.

The region is also well-known for its performance centers, Tanglewood and Jacob’s Pillow, which offer a variety of shows and events all year long but truly pop off in the summertime. Tanglewood is home to the Boston Symphony Orchestra, but musical performances there can span all genres. The fun part is that you can opt for pricier tickets with great seats, or grab cheaper ones on the lawn and bring a picnic. Jacob’s Pillow is great for dance performances, and theatre aficionados can check out Shakespeare & Company or the Williamstown Theatre Festival.

Most areas of the Berkshires are within a 20 minute drive, so it’s wise to choose one town as your base when staying here. The two most often-picked are Lenox and Stockbridge, which are both centrally located.

For the most charming stay, though, check out The Inn at Kenmore Hall which is in Richmond—just under 15 minutes away from Lenox. Owned by Scott Cole, formerly of the immaculately curated Monterey General Store, he and his partner, Frank Muytjens, the former head of menswear at J.Crew, were living in the area and restored a historic property with design elements that include many of their own decorative items collected over the years. Acres of private land are at guests’ disposal to explore along with a well-stocked bar cart and piles upon piles of coffee table books—and be sure to say hi to the couple’s dog, Dutch.

For those focused on wellness, head to the enormous Miraval Berkshires Resort & Spa. Its grounds feel more like a full community than a hotel, but that’s also because there’s so much to do there. The resort is very serious about relaxation, with a device-free policy to help guests unplug, but offers dozens of activities throughout the day—from guided hikes and archery lessons to cooking classes, yoga and Pilates, beekeeping and coffee workshops. It’s like an adult summer camp, essentially.

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