Art, Culture, and Classy Coziness on the NY-Connecticut Border

It seems like every New Yorker is looking for a weekend that involves nature, culture, design, history, good food, and a manageable driving distance. Sounds like a tall order, but it can all be found on the New York-Connecticut border.

NEW ENGLAND — In the mind’s eye, a weekend escape to New England should involve changing foliage, forested mountains, Colonial architecture, and starched, button-down shirts. Activities should include sitting in Adirondack chairs, relaxing beside a roaring fire, eating a fine meal surrounded by antiques, engaging in the natural world, taking in art at a leisurely pace, and daydreaming about living a peaceful, catered-to countryside existence — at least until it’s time to join the masses driving back to the city on Sunday night.

The embodiment of this exurban fantasy exists at a revived manor house on a private estate in bucolic Amenia, two hours north of Manhattan on the rural Connecticut border. You may have seen photos of historic Troutbeck — it reopened in 2017 under the detailed watch of Anthony and Charlie Champalimaud, who went after the place like preservationists; mom Alexandra Champalimaud’s design firm refurbished and outfitted the place with modern details that keep history intact. And the 18th-century property is truly legendary: As both a residence and an inn, it has hosted famous intellectuals, poets, naturalists, humanists, and also served as a meeting place for the early members of the NAACP. Thoreau, Twain, Roosevelt, and Martin Luther King Jr. have all been guests. The renovation makes the hotel feel like a lived-in private home, not a museum. It’s animated and lively, with sitting rooms, stone patios, manicured gardens, a babbling brook with hammocks swinging nearby, and doors wide open for children, artists, locals, large groups, private parties, posh millennials, and empty-nesters. (Read the full Troutbeck review we wrote when it opened.)

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My husband, toddler, and I checked in on the evening of an art opening and book signing of British artist Tim Braden, hosted by a friend. It was a civilized affair that meshed seamlessly with other casual gatherings in the parlors and with the dinner party crowd that amassed in the dining room. The inn has a gallery space and regularly installs art shows and hosts talks. The place feels very much like a gathering spot for locals and day-trippers, who can stop into the small restaurant for lunch or dinner, then retire to the living room with a nightcap and a game. I felt compelled to spend a few hours rifling through the library and then sitting with a stack of books on the upholstered fender near the fireplace.

Arts, Crafts, and Crusts

The understated intellectual tone at Troutbeck makes it a nice home base for exploring the local art scene, most specifically at Wassaic Project, a super-funky, DIY art cooperative operating from a not-well-insulated grain mill in the nearby town of Wassaic (pop. 1500). Despite the seemingly random location, the multidisciplinary arts organization draws artists-in-residence year-round, and hosts showcases, festivals, a haunted Halloween house, and an annual (very popular) art parade. We stumbled upon a free kid’s crafting clubhouse on the top floor of the seven-story space and found rows upon rows of bins filled (and labeled) with crafting materials, tables set up with various projects for kids of all ages, and open-ended toys for building, imagining, and creating. We spent a good hour or two cutting, gluing, coloring, and chatting with other kids, curators, and two lovely art assistants who happily helped our kid create (and then clean up!) after a rousing session of finger painting.

Across the way from the mill is a small print shop, bar, and pizzeria called The Lantern, operated by the same folks. The pies, we were told, are created by an alumnus of Brooklyn’s beloved Roberta’s. The Lantern also hosts live music events and pop-up Sunday brunches.

Natural and Architectural Marvels

Break up the ride to and from Armenia with a stop at The Glass House, designed by Philip Johnson as his own residence in the 1940s, in New Canaan, Connecticut. Tours, available from May through November, make their way through the main house, painting and sculpture galleries, and a one-mile walk over grassy paths. Advance reservations are required and kids under ten are not allowed. Fortunately, design junkies with smaller children can get their fix at nearby Grace Farms, a fascinating non-profit center on 80 acres of fields and woods punctuated by a $67-million-dollar building known as the River, a curvaceous structure built of steel, concrete, wood, and glass that meanders through the landscape. Built by acclaimed Tokyo-based firm Saana, the building is a thing of beauty that brings the outdoors in and the indoors out. There’s a peaceful library, a bright cafe and tea pavilion, a craft center, a gymnasium, and a light-filled sanctuary/indoor amphitheater for programming that runs the gamut — philosophical, religious, scientific, nature-based, and social justice-oriented. It's free and open to the public six days a week and makes for a beautiful place to stop and stretch your legs any time of year.

Plan Your Trip

A car is best for exploring the area at your whim. Ubers are harder to come by, but taxi services can be arranged in advance. If traveling by train to Troutbeck, get off at the last stop on the Metro-North Harlem line. The ride is a little over two hours.

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