A wintertime party at Stissing House. | Sara Wallach
Captain Cornelius Elmendorf built his tavern and inn in 1782. It served Pine Plains, New York, when the Hudson Valley hamlet was a busy crossroads. Main Street bustled with rail lines, and the town boasted a vaudeville theater and an opera house. During World War I, the rail lines were torn up and repurposed into ammunition, sending Pine Plains and the tavern into decline. In 1995, the building reopened as a French restaurant under Michel and Patricia Jean, operating until 2021 when the owners moved on to open Champêtre nearby.
That’s when Clare de Boer stepped in to open Stissing House. The chef behind King in Soho was among the many who decamped from the city during the pandemic, settling with her family in Dover Plains. When the nearby Pine Plains historic building that houses Stissing House came up for lease in 2021, she had no plans for a Hudson Valley restaurant — until she walked through the door.
Since opening in March 2022, Stissing House has become a destination that draws diners from around the state to a town of less than 2,000 people. De Boer (who recently signed on as a contributor at CBS as part of Bari Weiss’s divisive shakeup at the network) once again turned the restaurant into a buzzy tavern, where the food happens to be quietly excellent.
“[De Boer] described it as a rocking ship, a party,” says general manager Katie Pearce, who has lived in the Hudson Valley for nearly a decade and joined Stissing House when it opened. But Stissing House also represents a return to the building’s roots, making the lively, slightly chaotic destination “a place where people really come to be together,” Pearce says. “I felt an immediate connection.”
The vibe
The 6,000-square-foot building divides diners into multiple smaller rooms, including a second floor for private events. Meals require a promenade around the stately building, which includes wide-plank floors, exposed beams, and multiple fireplaces. You might start with cocktails in the Woodshed Lounge. Then comes dinner in the main dining areas, which include the Games Room, the Drawing Room, and the Tavern Room. Upstairs, events are held in one of the few remaining early American domed ballrooms in the country.
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What to order
Pearce’s favorite way to start on a wintry night is a house gin martini, which is finished with a spritz of fir and a grapefruit peel garnish. “Even in the middle of winter, people still want it. It kind of breaks the rules,” she says. In the colder months, pair it with broth, dark and savory, made from roasted beef bones (sometimes layered with duck or chicken) and winter herbs. Other snacks include roasted oysters, smoked ham and pickles, and malt vinegar potato chips.
For a late winter dinner, Pearce suggests the chicken liver mousse that’s “super creamy,” thanks to a lot of butter. It’s paired with oversized wood-oven-baked crackers pressed with rosemary and sea salt. “The crackers are really light,” she says. “You need that contrast.” She likes it with a pour of tawny port. During this cold season, citrus is the brightness on the plate — be sure to order both the winter citrus with mint and endive, as well as a chicory Caesar with sunchokes.
Throughout the year, look for salads like endive and pear with buttermilk dressing, or frisée and lentil with pheasant egg, depending on the season. Spring menus have featured wood-fired bread with asparagus and goat’s curd, while summer brings tomatoes, corn, and basil.
The most talked-about dish at any time of year is the dramatic savory pie for two. It rotates seasonally through options like rabbit, fish, and steak-and-ale. “It always feels like what you want to eat right now,” Pearce says. The current venison pie with sherry has a deeply browned, barbed crust, a bone and marrow tucked inside, and comes with a pot of mashed potatoes for two placed on the table alongside it. The homey presentation on a pie plate is half the fun.
After dinner, retreat to one of the fireside lounges for a large-format meringue tumble, in which towers of meringue and preserved fruits, like raspberry and lemon curd, fill a giant bowl. “It’s meant to be messy and beautiful,” Pearce says. Other desserts include the restaurant’s signature coconut cake, and summer brings offerings like strawberry cobbler with chamomile ice cream for two.
When to visit
If you’ve only ever thought of the Hudson Valley as a summer or leaf-peeping destination, Pearce would encourage you to rethink your timing. “We really do embrace all seasons here,” Pearce says. That philosophy shapes how she suggests first-timers experience the restaurant — especially in late winter, when the Hudson Valley feels quieter and more introspective. “You don’t have to wait for summer to come,” Pearce says. “There’s something really special about being here when it’s quiet outside and warm inside.”
How to book
Reservations are available through Resy and recommended, though walk-ins are welcome. The restaurant is open Monday, Thursday, and Sunday from 5 to 9 p.m., and Friday and Saturday until 9:30 p.m. Book in advance, especially for weekend dinners, though last-minute availability sometimes opens up.
How to get there
Pine Plains is about 100 miles north of Manhattan, roughly a two-hour drive via the Taconic State Parkway. From NYC, take the Henry Hudson Parkway north to the Saw Mill River Parkway, then connect to the Taconic north to Route 199 east. You could stop at Magazzino to check out its contemporary Italian art and grab lunch at Cafe Silvia inside. Another option is a stop in Beacon at Ziatun for Eastern Mediterranean fare, or Meyer’s Olde Dutch for burgers. From Washington D.C.,expect about 4.5 hours via I-95 north through New York City, or opt for the slightly longer but more scenic route via I-84 through Pennsylvania. The drive from Boston takes about 2.5 hours via I-90 west and the Taconic south. You could stop for lunch in Leeds at Gracie’s Luncheonette or Briskette and Birdee in Canaan along the way.
By train, take Amtrak to the Rhinecliff Amtrak station (RHI), followed by an Uber for just under 20 miles.
Where to stay
While Stissing House is no longer an inn, there are a handful of Airbnbs nearby. There’s also a more decadent stay at the 250-acre Troutbeck about 15 miles away. For a more intimate experience, try the the Inn at Pine Plains, which features eight uniquely decorated bedrooms, some with kitchenettes, and serves a continental breakfast.
What else to do, see, and eat around Pine Plains
Consider the Stissing Mountain Fire Tower, a 1.8-mile hike with spectacular views from the 90-foot climbable tower. Thompson Pond Preserve offers easier trails and good birdwatching. The Stissing Center hosts chamber music and theater performances in a restored 1915 building. The Culinary Institute of America and its restaurants; Springwood, the estate of Franklin D. Roosevelt; the walkway over the Hudson in Poughkeepsie; and Dia Beacon are all within a reasonable drive as well.
To make your trip truly food-filled, don’t miss Chaseholm Farm Creamery for artisanal cheeses or Ronnybrook Farm for other dairy-based goods. And don’t forget Champêtre, the restaurant that used to inhabit Stissing House’s historical building, for French bistro fare.