Who Knew? An Hour Away, a World Apart

‘Who Knew?’ is sponsored by Walter Stewart’s Market.

Use a compass, if such a thing still exists, to draw a circle with a one-hour driving radius around New Canaan. You’ll find our little town sits squarely within striking distance of wildly divergent energies. With the traffic gods on your side, you can get to a Michelin-starred tasting menu in Midtown or a clam shack up the Connecticut coast. Yankees or Mets, Giants or Jets, New Haven apizza or a Central Park cart dog—the point is, our location is a prime launchpad for discovering the best of what’s out there. And also New Jersey.

One of my favorite directions to launch myself is northwards, to Litchfield County. Technically, it’s only about 40 miles away, but somehow it feels like I’ve flown a single-engine Cessna right through the space-time continuum back to a quieter, less distracted existence. Whether you visit for an afternoon or an entire week of swim-read-eat-repeat, the effect is the same: time slows, blood pressure drops, and the signal-to-noise ratio improves dramatically. It’s quiet. It’s unspoiled. It’s deeply restorative. It is (mercifully) largely untouched by lifestyle influencers. And there’s culinary gold in them thar hills.

 

Orienting yourself: 

The Litchfield Hills served as a strategic resupply point during the American Revolution, and have since remained a culturally important hub for art, education, and progressive thought. To wit: the town of Litchfield was home to the country’s first law school. While the area has a decidedly rural feel–indeed, a few of the vendors at our Farmer’s Market commute down from Litchfield County–it’s also a longstanding country retreat, with tucked-away pockets of Brunello Cucinelli-level quiet luxury and lovely lakeside retreats. 

 

While flashier aspirants might commit tax fraud for the sake of a summer Hamptons rental, certain New York-area families have kept country houses in Litchfield for decades. During the pandemic, its real estate market boomed stratospherically, and suddenly, it seemed that half of my previously “Brooklyn-or-nowhere” marketing colleagues had bought a house in Washington or Woodbury from which to Instagram their hydrangeas. As one does.

Some towns are tonier than others, so if you’re clout-chasing, head to Washington, Litchfield, Kent, or New Preston. Lakeville and Salisbury, located way up north, boast beautiful vernacular architecture and well-known boarding schools. Roxbury has been home to literati and glitterati for decades–we once rented a house that had been Candace Bushnell’s, across the street from another where Arthur Miller lived with Marilyn Monroe, and around the corner from Alexander Calder’s studio-farmhouse compound. But the part that impressed my husband the most, obviously, is that Walter Matthau once owned the house up the street. 

But the beauty of Litchfield isn’t in its résumé. Unlike Miami—or even Montauk—it’s not about being seen. It’s about disappearing, perfectly, into your own personal flavor of seclusion and staying put for as long as humanly possible. And, of course, giving your nervous system a much-needed break from the incessant din of gas-powered leaf blowers. 

As one does.

 

Where to stay?

The Mayflower Inn & Spa was my gateway drug to Litchfield County – Andrew and I went up for a birthday weekend a decade ago and immediately fell in love with the area. The 30-room inn has since undergone an interior refresh by Celerie Kemble, brightening up the dour patrician vibes with cheery eclecticism, if deploying a somewhat critical mass of pampas grass. Still, it’s an antique charmer with a delightful yellow game room and great cocktail list, and the truly excellent 20,000-square-foot spa might just cure what ails you.

Lately, we’ve been renting houses up there for a week at a time, bringing our three Labradors to live their most countrified lives. Posh Pads is a great resource. Airbnb is… less so. I’ll just advise this: if “bucolic bliss” is promised in a property’s headline, run the other way. It’s code for “you could shoot the last scene of The Swimmer here.” It was a costly mistake that I made this year, and one that I will not make again. 

 

Where to eat? 

Here’s where this article gets fun, and probably why you’re reading it. There are dozens of top-notch places to eat in Litchfield County, ranging from fancy-farmy multicourse prix fixes to the humblest hamburger stands. I’ll spin you quickly through our favorites in three fairly unscientific categories, so you can hit the road and start checking them off. 

Non-negotiables:

Tables here can be tricky to score with little notice, but a meal at New Preston’s Community Table is worth the work. Chef Bolivar Hilario’s ethereal, seasonal cooking haunts me, visit after visit, until we return. The space is calm and arty, the cocktail list is inventive without being too precious, and the staff is always ready with a fantastic recommendation. You KNOW you’ve got a great server when he cops to falling down YouTube wormholes about the Japanese luxury melon market. At Community Table, you get the sense that everyone in the building just really loves food, and if you’re a food person, you’ll feel you’ve arrived in the right place. 

 

We recently feasted on lobster Fra Diavolo pasta, grilled stone fruit over stracciatella, a mushroom tlayuda, and gazpacho made with heirloom tomatoes, Jimmy Nardello peppers, and rosettes of spectacularly sweet cantaloupe. Can gazpacho be so good, you see stars? Because I did. Summer produce shows up and does the most on this menu, because when you’re within corn-shucking distance of actual farms that might grow it, it sings.

P.S. A Monday night cheeseburger night brings locals out of the woodwork. 

Speaking of cheeseburgers, two roadside stands deserve a spot on the shortlist, because roadside hamburger stands are a vanishing breed and one of the most unequivocally delightful ways to eat a summer meal: the Gooseboro Drive-In in Bantam, and Clamp’s in New Milford. Get a Hummel red hot with chili at Gooseboro, and get a burger with fried onions, accompanied by a side of salty onion rings, at Clamp’s. Per my friend Jean, who’s been eating at Clamp’s since she was a (lucky) kid: “it’s nothing special, and it’s everything special.” Sit at plastic chairs and watch the world whizz by. Long live the world’s roadside burger stands, and long live our arteries so that we may support them. 

 

Heavy hitters:

We all already know that a pair of Manolo Blahnik executives hatched the world’s best business diversification strategy: a gentleman’s farm in Bantam. Their ice cream and prizewinning cheeses are available at Walter Stewart’s year-round, and I don’t let the holiday season pass me by without a bottle of their spectacular eggnog. Up in Litchfield County, they also operate a couple of restaurants: Arethusa Al Tavolo is this empire’s fine dining outpost. Service is flawless, and the menu is quite good (tempura squash blossoms forever!), but you’ll be as cheek-to-jowl with Blahnik looky-loos as if you were in the West Village. It’s a great place to get a sense of place, but if you’re time-starved, the ice cream scoop shop next door gives the dairy’s offerings their fair due. 

Open seasonally, Ore Hill in Kent is about as direct as a farm-to-table dining experience can get, and their five-course tasting menu is something everyone must sit down to at least once. The building–a capital T-tastefully restored 1781 farmhouse–is beautiful on its own. Inside it, alchemy transforms produce from nearby Rock Cobble farm into blink-and-you’ll-miss-’em seasonal dishes you’ll dream about, and probably never taste again. If you go in midsummer, you’ll find the purest expression of whatever the team has picked that day. Give yourself time to wander around Kent afterwards; this is a meal you’ll want to both talk about and walk off. 

 

Litchfield’s Materia Ristorante is another we return to each year. The room’s graceful proportions and excellent service would be reason enough, but I keep going back with the knowledge that I will find what I seek at the end of every rainbow: a plateful of housemade pasta. Last week, it was the labor-intensive dish that our collective pandemic boyfriend Stanley Tucci made famous: Spaghetti alla Nerano, sauced only with fried zucchini, basil, and cheese. As millions of nonnas knew before us, love and time transform Italian cooking into infinitely more than the sum of its parts. 

Another unforgettable Materia dish was my husband’s eggplant parmigiana appetizer. It wasn’t the breaded-and-fried Italian American staple we’d expected, although we’d never have been mad at that. It was a many-layered terrine with silky, paper-thin sheets of eggplant interlaced with ribbons of basil, mellow tomato sauce, and a restrained quantity of mozzarella di bufala. Unbelievable. I would gladly bring a picky vegetarian to this restaurant; the veg dishes aren’t an afterthought, but rather a boisterous celebration of all the wonderful things the short Northeastern growing season can accomplish.

 

Casual spots:

Downstairs from Ore Hill, you’ll find its casual but no less noteworthy sister, pizza spot Swyft, and once you find it, drop a pin for return visits. The menu is simple but full of hot, hot hits. A crisp, lightly dressed leafy salad that snaps with freshness. Supersoft, caramelized, honey-roasted carrots that, even if three meager carrot coins remain on the dish, you will take home as leftovers and eat with your fingers before going to bed. Pizzas, which are the star of the show, are made from a 37-year-old sourdough starter and topped simply, but commendably. Ours had sauce made from San Marzano tomatoes, housemade mozzarella, sopressata salami, honey, and Aleppo pepper. It was exquisite.

The Owl, located in adorable, tiny New Preston, also serves artisanal pizza and offers an excellent wine list. Ask to be seated in their charming outdoor garden and try not to eavesdrop on your table neighbors, unless they’re fascinating old locals or UES hard chargers on furlough, both of which show up here in abundance. On a recent visit, we couldn’t resist a pastrami sandwich from their menu, and we were rewarded with perfectly spiced pastrami, sauerkraut, grainy mustard, and melted cheese. 

 

In the morning, head to The Po Café in Washington (located in the same building as the town post office, out of some zoning board commitment to being adorable at all times) and load up on specialty iced coffees and breakfast sandwiches. I like the Po Taco (scrambled eggs, chorizo, tater tots). Still, there’s a Po Crunchwrap (a gourmet breakfast recreation of Taco Bell’s Crunchwrap Supreme) that would successfully address even the hangriest of appetites. 

* * *

Of course, Litchfield has hikes, museums, gardens, clubs, wineries, and distilleries to experience. But I always remember the food best. I hope you’ve enjoyed this Litchfield County roundup, and that it inspires you to hit the road, whether for a day trip (here’s a playlist for your travels!) or a more extended stay. 

Next month, I’ll be back visiting haunts closer to home. But for this moment of summer, appreciate this state’s graceful northwest corner, watch the pastures and fields slip by on your languid drive to dinner, and get yourself a good roadside burger. New Canaan will be waiting for your return with abundant parking (a girl can hope, right? I’m a fan of the new plan!) and open arms.