Even though plenty of New Yorkers might claim you can do anything you want without ever leaving Manhattan, I’ve found that I appreciate the conveniences and culture of the city so much more after some time with nature.

My boyfriend grew up on the Upper West Side, spending summers at a lake house in the Berkshires. He’s introduced me to the art of the “upstate weekend” and we’ve been working to perfect it in all its forms: the Interlaken Inn, a family friends’ 1860s-built house with a slightly more modern swimming pool, and a quaint house with its own lake access.

Phone service is spotty, internet coverage is impossible. Even without a defined schedule, the day seems to fill up quite easily with activities. There’s reading by the lake, canoeing around the lake, swimming across the lake. Maybe pop over to Hotchkiss School to squeeze in a few sets of tennis, play nine holes at Egremont Country Club or put up the badminton court on the lawn. Once the sun sets, there are campfires to build, marshmallows to roast, s’mores to make.


A sprinkling of small towns is scattered along the New York, Connecticut and Massachusetts borders: Lakeville, Millerton, Egremont, Great Barrington. They’re quintessential American towns, with Main Streets and colonial architecture and family-owned businesses.

“Every weekend away feels like a refresh button on life in the city: I come back feeling rejuvenated and ready to enjoy everything the city has to offer.”

The Berkshires is an easy two-hour drive from Manhattan: the route lacks Hamptons traffic, boasts lakeside views and features a roadside stop with burgers and soft-serve that rivals Shake Shack. It’s still hard for me to believe that so much greenery, open space and open skies can exist so close to the chaos and concrete of Manhattan. Every weekend away feels like a refresh button on life in the city: I come back feeling rejuvenated and ready to enjoy everything the city has to offer—at least until the next trip upstate.

Although I’ve been enjoying the escape from summer humidity, the Berkshires is also an excellent autumn destination: time your visit for that sweet spot in late September to early October when the leaves are changing into a thousand golden hues of crimson.


STAY: There are plenty of lake houses to rent and family-run bed-and-breakfasts in the area, but I’m partial to Interlaken Inn. The rustic resort is a sprawling campus with a variety of room choices with either hotel or apartment amenities. There’s a pool, tennis courts, basketball court, swing set, a game room with billiards and air hockey—even a salon and spa! It’s located right across the street from the lake for swimming and rowing. A popular destination for weddings or family vacations, the clientele runs the gamut—because who doesn’t love a lush backdrop of greenery and some games in the fresh air? And if you can’t quite leave the trappings of city life behind: they’re dog-friendly, can bring you breakfast in bed AND have excellent Wifi.

EAT: In many ways, it’s Brooklyn 2.0 out here: fancy farmers markets, organic provisions shops, CSA memberships where you pick the peas straight from the fields. The best place to splurge on all of that local, seasonal goodness is John Andrews: it bills itself as the original farm-to-table restaurant, with a vegetable garden growing right outside. Last time I visited, I spotted zucchini flowers on the stalks near the parking lot and ended up having zucchini flowers baked and stuffed with ricotta and honey for my starter. ‘Twas divine.


DO: The Appalachian Trail runs right through the area (if you haven’t read Bill Bryson’s A Walk in the Woods, do it now!), and it’s easy to hop on the trail for a day of hiking. Whether you want an easy stroll from the parking lot or a more strenuous hike, the stunning Bash Bish Falls is worth the walk. Straddling the state line of Massachusetts and New York, it’s technically the highest single drop waterfall in Massachusetts.

DRINK: It’s not quite Napa Valley, but Millbrook Winery pours some wonderful wines in a picturesque setting. Tours, tastings and gorgeous views are available daily—just make sure to bring along a designated driver, as the single-lane roads to reach the winery are beautiful but curvy.

DON’T MISS: The Red Rooster is an institution on Route 22 from New York City to the Berkshires: the cult favorite drive-in has been serving up burgers and milkshakes for more than 50 years. No matter what time of day it is, it’s always the right time for a cherry dip soft serve (with sprinkles!). With picnic tables, clean bathrooms, a big lawn, an arcade and a mini-golf course, it’s the ideal roadside stop for all ages.


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