My partner and I were lucky enough to visit the Berkshires—the picturesque region in western Massachusetts known for attracting writers, musicians, artists, and those looking for respite among the mountains—while the autumn leaves were still high in the air.
We drove up from New York City in the INFINITI QX60, a spacious, seven-passenger luxury SUV, complete with Zero Gravity seats, made to keep long drives comfortable, and a Bose Performance Series 17-speaker sound system—the kind of features you come to appreciate when navigating a weekend road trip. With the heated seats (and steering wheel) cranked, we watched as the passing trees put on a show, showing off in swaths of bright yellow and cherry red.
But no matter what time of year you choose to visit the Berkshires, there’s magic to be found—whether within MASS MoCA, the sprawling contemporary art museum; atop Mount Greylock, the highest point in the entire state; or at a local eatery like No Comply Foods, where a baby pink building on the side of the road houses a menu of excellent dishes, nearly all for under $20. Ahead, find even more of what to see, eat, and drink during your next stay up north.
What to See
MASS MoCA
Lace up your walking shoes. The impressive Massachusetts Museum of Contemporary Art, otherwise known as MASS MoCA, is housed in a converted factory complex—which means, to see all the pieces on the expansive campus, you’ll have to walk from building and building and from floor to floor. (Not to mention, there are several outdoor works.) You can wander the space on your own—stopping to see Sol LeWitt’s giant colorful walls or James Turrell’s experimentations with light—or pop by the lobby for a one-hour guided tour that will show you some of the museum’s highlights. MASS MoCA is unique in that it does not have a permanent collection, so chances are, there will always be something new to see.
Mount Greylock State Reservation
Savor the changing leaves (or the bright greenery or the sharp winter air) while traversing the woods of Mount Greylock State Reservation. If hiking is less your speed, simply take a windy drive up to the top, which also happens to be the highest point in the state. Just be sure to account for congestion during super busy fall weekends.
Hilltop Orchards
If you’re in the Berkshires to check off a bucket list of seasonal activities, swing by this 200-acre orchard. Walk along the trees and pick your own apples, try one of their “orchard-to-can” hard ciders (I’d recommend the original), indulge in a wine tasting, and most importantly, grab a few of the best apple cider doughnuts I’ve ever tasted.
The Great Countryside Fleece Pullover
FP Movement Let’s Bounce Pants
Salomon Xt-6 Gtx
Where to Eat
Mezze Bistro and Bar
Save one evening of your Berkshires trip for a reservation at Mezze Bistro and Bar. You’ll be seated in a simple, understated dining room and offered a menu from which to pick your three-course prix fixe meal. The farm-to-table dishes change seasonally, but if they’re offering the brothy bean ragout or their take on sunchokes—a creamy, crispy starter inspired by patatas bravas—add them to your order. End your meal with the chocolate espresso budino, complete with flaky salt and airy whipped cream, and a fall-tinged fig sour cocktail.
No Comply Foods
No Comply Foods is the type of restaurant you hope to stumble upon on vacation. Inviting on the outside (the building is literally painted baby pink), slightly quirky on the inside, with stellar dishes and a community vibe, it’s the kind of place that makes you feel like maybe you’re a local, too. Started by a husband-and-wife team—the former, Stephen Browning, was previously a chef at Brooklyn’s Marlow & Sons—the brunch and dinner spot is straightforward: You order at the counter from a small, changing menu; pick an open table; and bus your plates when you’re done. It’s the food that’s the star. Opt for the Turkish eggs surrounded by velvety labne, bright chili crisp, and soft Japanese sweet potato. And don’t miss the Pac-Man machine in the back.
The Farmstead Creamery at High Lawn Farm
Pack your Lactaid for this one. At The Farmstead Creamery at High Lawn Farm, you can order a “farm-to-cone” ice cream, a perfect grilled cheese, or a customizable charcuterie board to enjoy at the picnic tables on the dairy farm’s quaint grounds. (You can also purchase a number of products in order to repeat the experience at home.) Just don’t leave without paying a visit to the calves in their nursery.
Dunst Blouson Leather Jacket
Reformation Tate Regenerative Wool Sweater Dress
Calzedonia 50 Denier Total Comfort Soft Touch Tights
Where to Drink
The Airport Rooms
The vibes are right at The Airport Rooms, the farmhouse-turned-cocktail lounge and restaurant. Inside, a handful of cozy, vintage-inspired nooks will make you think you’re knocking one back in your cool aunt’s living room—unless the weather is nice, in which case, you’ll be headed to the backyard patio. Sip on a glass of the Currant Affair, a mezcal drink made with blackcurrant liqueur, blackberry, and lime. To nibble, get the grilled carrot salad. And the smoked mozzarella arancini. Maybe the brownie, too.
Berkshire Cider Project
It’s all in the name. Stop by the Berkshire Cider Project tasting room and bottle shop to try their locally made collection of dry hard ciders. (And, if you feel so inspired, maybe sign up for their Cider Club.) Founded by a husband-and-wife duo, the establishment is located inside Greylock WORKS, a former cotton mill repurposed to serve the community. After you grab a glass of sparkly cider, you can visit the on-campus shops, restaurant, or distillery.
Hot Plate Brewing Co.
A favorite of The New York Times, Hot Plate Brewing Co. is a Latina-owned seven-barrel brewhouse and taproom that serves craft beer, wine, coffee, tea, and baked goods, all in the hopes of offering a safe third space to the community. The two founders started as homebrewers and have channeled their love for making beer (the menu includes a “bold and chocolatey stout” and a blonde ale brewed with chamomile) into a business that also gives back; through Hot Plate Brewing Co., the duo raises money to provide heat for eligible households in the area.
Rumored Yellowstone Jacket
Guizio Rowan Tartan Dress
Tony Bianco Fantasy Chocolate Nappa
Where to Stay
TOURISTS
TOURISTS bills itself as a riverside retreat, an apt description for the motor-lodge-inspired hotel that features a warm lobby (fireplace and snack menu included); fire pits; walking trails and outdoor sculpture art; a pool for summertime; delightful breakfast you can order to your door every morning; and in-room radios with a playlist so good I asked the staff about it before checking out. Touring musicians often stop by to play free, stripped-down sets, and TOURISTS’s cocktail lounge, The Airport Rooms (see above), is a short walk from the main property. So really, why ever leave?
The Inn at Kenmore Hall
This intimate six-room inn is more like a home away from home than it is a hotel. The house was first built in 1792 and has served a number of purposes since, including acting as a former boarding school. Now owned by partners Frank Muytjens, who previously headed up J.Crew menswear, and Scott Edward Cole, a restaurateur and artist, the lovingly decorated Inn at Kenmore Hall includes a blooming kitchen garden, several communal living spaces, 20 acres prime for exploring, and made-to-order breakfast in the morning.
Canyon Ranch Lenox
If you’re hoping to head to the Berkshires for a luxurious wellness getaway—or maybe have some particular health issues you’re trying to target—Canyon Ranch Lenox could be your place. Located on a historic 19th-century estate, the resort offers a rotating menu of workout classes, spa treatments, cooking tutorials, mindfulness workshops, outdoor adventures, and more (read: live musical performances and a bingo night), so you can choose your own adventure. Maybe one day it’s early-morning yoga and a deep-tissue massage and the next it’s traversing the ropes course and receiving a tarot card reading. Relax fully, focus on fitness, or consult their on-site health experts—whatever you need to leave the property feeling recharged.
NAKEDCASHMERE Darya Longline Cashmere Cardigan
NAKEDCASHMERE Carolina Crewneck Cashmere Tank
NAKEDCASHMERE Anastasia Wide Leg Cashmere Pant
Beauty Picks
Dae Fairy Duster Dry Shampoo
Refresh your post-hike hair with a few pumps of this oil-sapping dry shampoo powder. A multi-tasking wonder, this product also boosts volume and nourishes via a blend of prickly seed oil and botanical extracts.
Rabanne Fresh Touch 24H Radiant Foundation
One touch is all you need for subtle coverage. However, the beauty of Rabanne’s skin tint is revealed in layers—add a few more droplets to build a hydrated, even-toned veil for a filter-like version of yourself.
111SKIN Cryo Revitalising Moisturiser
Skip the cryotherapy appointment and add this cooling moisturizer to your travel lineup. Featuring 11 forms of hyaluronic acid, this weightless moisturizer feels like a splash of cold water on stressed, dehydrated skin.
