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A trip to Massachusetts isn’t all about Boston, okay? In fact, a trip to the Berkshires effectively serves as an antithetical experience to the state’s capital. The region, only about three hours away from NYC, is an idyllic dream at any time of the year with winding, picturesque streets, charming properties and first-class restaurants.
The fun thing about the Berkshires is that it really feels like an escape from what NYC is, which also made it a popular destination for some of America’s most famous literary figures. The region is particularly ideal for outdoor adventures, which is why autumn is one of the most popular times to visit for indulging in world-class leaf gazing and more.
Regardless of the time of year, the Berkshires offer 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 go.
Discover the incomparable natural landscape
First and foremost, it is important to describe what the Berkshires are exactly. The region is technically known as Berkshire County and is the westernmost county in the state. As part of the Appalachian Mountains, the entire area is embedded in the Taconic Mountains, the Housatonic River and the Hudson Highlands. Don’t expect dramatic peaks, however, as the route is much more rolling than rocky.
Like many New England destinations, the Berkshires are a true reflection of the seasons. In winter you can expect powder snow and an influx of skiers, while autumn brings a splendid blaze of colors. As you drive through the region in the spring and summer, you’ll see fields of goldenrod and other wildflowers breaking through the green and blooming along the hills.
Escape the chaos of city life for rolling mountains
The Berkshires are, in a way, the answer to the Hamptons in western Massachusetts. There’s no way to gloss it over: it’s a bougie place to vacation. While the two go together in terms of charm and imagination, they definitely differ in their attitudes. Aside from the fact that the Berkshires don’t have a beach (pose the classic question that pits beach people versus those who prefer the mountains), it’s also far more low-key.
As a laid-back destination, it’s good for a weekend getaway with a good bottle of scotch and good friends, rather than a night of partying on the town like you might enjoy in Montauk. It makes sense when you consider that the area was made famous in part by literary figures who escaped their otherwise hectic city life for pastoral splendor. Here they bought estates (called cottages) that look more like castles – many of which can still be visited today.
Take a hike (or take a walk)
There are countless opportunities to experience nature in the region, which have a wide range of levels of difficulty, from the well-groomed Berkshire’s Botanical Garden for pleasant strolling to climbing Mount Greylock for a day hike. For those looking for a sweet spot between the two, hikes to places like Olivia’s lookout point are perfect. At the beginning, look out for the signs to also take part in a self-guided mindfulness hike that begins with an audio meditation to ground yourself.
Another local favorite is Bash Bish Falls which can be reached on foot from two different states. It is less than a mile to hike the falls from Massachusetts, and about a mile and a half from New York. In any case, reward yourself with the sight of two waterfalls that diverge around rocks and meet in a large pool below. Swimming is unfortunately not allowed, but definitely worth a visit.
You can also find natural splendor at Natural Bridge State Park, where you can see the only white marble arch in North America, carved out of glacial melt over 13,000 years ago.
Feast in a locavore restaurant scene
Farm-to-table dining fans will find their home in the Berkshires, where fresh, seasonal produce is pretty much the name of most restaurants. Prairie whale, opened by Mark Firth of Marlow & Sons in Brooklyn, has an expansive deck with ample lawn seating and uses local produce to create its menu – some even come from Firth’s own farm. Pasta restaurant is another local favorite with a menu that changes daily.
For a more historical and unique experience, this offers Old inn in the countryside is off the grid and completely lit by a candle. The Red Lion Inn is with the locals as a typical Berkshire experience with tons of. known Telling stories. Take a seat in the Main Dining Room with New England classics or in the more rustic (and family-friendly) Widow Bingham’s Tavern with burgers, homemade chilli and lots of pints. For Vietnamese dishes, Truc Orient Express has been a constant for more than forty years. Xicohtencatl offers authentic Mexican cuisine; the Italian-American menu from Francs also includes vegan options; and Berkshire Mountain Bakery has breads and bestsellers like their oatmeal pecan biscuit.
Let yourself be inspired like famous writers
Visitors to the Berkshires have always been inspired by these unique landscapes, even the famous author Herman Melville, who loved his vacation so much that he eventually decided to move. At one point he had a literary blind date with another writer, Nathaniel Hawthorne, who wrote “The Scarlet Letter,” and the two rose Monument mountain together near Lenox. Allegedly, during this hike, Hawthorne gave Melville advice on which direction to take with the book he was working on – a little-known novel called “Moby Dick.”
Explore the arts and culture at the Norman Rockwell Museum and the homes of legendary American writers
Today you can end your hike on Monument Mountain and head straight to Melville’s house called. travel Arrowhead. It is located in the town of Stockbridge, which is where you will find the Norman Rockwell Museum. Rockwell became famous for his paintings and illustrations depicting American life, and his longtime residence is what he once called his “best studio yet.” The museum hosts 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 mountain, which once lived the respected author Edith Wharton Рthe first woman to win the Pulitzer Prize for Literature. Located in the town of Lenox, it is a huge property created as a more practical American take on European mansions. Here you can have lunch in the terrace caf̩, explore the premises of the property and stroll through the beautiful grounds.
No trip to the Berkshires is complete without one of the largest contemporary art museums in the country, the Massachusetts Museum of Contemporary Art, or MASS-MoCA. The vast inventory of works spans 250,000 feet across 19 galleries in a renovated 19th century factory whose industrial campus was expanded in 2017.
The region is also known for its centers of excellence, Tangle and Jacob’s pillowwhich have a variety of shows and events all year round but really jump off in the summer. Tanglewood is home to the Boston Symphony Orchestra, but musical performances can span all genres. The fun part is you can opt for more expensive tickets with great seating or grab cheaper ones on the lawn and bring a picnic. Jacob’s Pillow is great for dance performances and theater lovers can watch it Shakespeare & Company or the Williamstown Theater Festival.
Stay in some charming digs
Most areas of the Berkshires can be reached within 20 minutes by car, so it is advisable to choose a city as a base for your stay here. The two most popular choices are Lenox and Stockbridge, both of which are centrally located.
However, for the most charming stay, be sure to check out The Inn at Kenmore Hall which is located in Richmond – just under 15 minutes from Lenox. Owned by Scott Cole, formerly the immaculately curated Monterey General Store, he and his partner Frank Muytjens, the former J.Crew menswear manager, lived in the area and restored a historic property with design elements that incorporate many of their own decorative items collected over the years. Morning private land is available for guests to explore along with a well stocked bar cart and stacks of coffee table books – and say hello to the couple’s dog, Dutch.
For those who are focused on wellness, visit the huge one Miraval Berkshires Resort & Spa. The grounds feel more like a whole community than a hotel, but that’s also because there’s so much to do there. The resort puts a lot of emphasis on 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 essentially like an adult summer camp.
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