During the Revolutionary War period, Pine Plains was more bustling than today’s quiet hamlet suggests. At the crossroads of major routes and two rail lines, it hosted hundreds of visitors daily, and at the center of that activity was Stissing House. Completed in 1783, it had a tavern, rooms for travelers, and a domed ballroom for dancing.
Over the last 250 years, Pine Plains has boomed and busted, and Stissing House has reflected those fortunes and hardships with its own crests and troughs. In 2025, the Hudson Valley is thriving, much of its energy derived from lauded restaurants that draw on nearby bounty, and Stissing House finds its place among the most elite of these.
Since 2022, acclaimed chef Clare de Boer has been the proprietor of Stissing House. Having big dreams but modest expectations, de Boer opened the restaurant “with a very clear vision that has blown up and grown with this excellent team.” Describing Stissing House as a playground with a building that has so much to offer, she says, “We can dream things up, throw them into the community, and see what sticks.”
With Nathan Rawlinson (General Manager), David Nathans (Chef de Cuisine), Katie Pearce (Director of Feasts), and Pom Shillingford, who adds beauty to the interior with native flora—this week’s vases held foraged wild parsnip and Queen Anne’s Lace, de Boer has revived Stissing House—not just as a restaurant but also as a community hub.
Large upstairs rooms host monthly feasts and private celebrations. There’s a music series, crafting lessons, Easter egg hunts, and pizza parties for kids. Look out for cooking classes later this year and a sweet-and-savory contest for pie season in November.
Proud of its storied past, nothing is square, level, or plumb at Stissing House —and everyone seems to like it that way. The parlor, made for the cozy months, centers on an open fireplace with a picture-perfect log balanced on an andiron. Warm wood is complemented by unbleached whites and tapered candles with actual flames in simple, iron holders adorn nearly every surface.
At the bar, Shaker chairs sit beneath exposed beams with the dining room and brass beer tap reflected in a narrow beveled mirror.
Now, as back in the 18th century, the tavern is the center. Wood-fire cooking guides the menu, so even in summer, the food leans hearty. Broth, spit-roasted rabbit, roast chicken, fish, potatoes, and fish pie are all on offer mid-summer.
Snacks include oysters, pickles, ham, and gouda. When we dined at Stissing House in July, we chose house-made chips—curly, salty, and light—overflowing their vessel. It’s impossible not to make a bit of a mess, which seems entirely the point. Cocktails are traditional with a twist. The Pine Plains Martini ($19), served in vintage etched glass, includes a touch of fir. A Tropical Monopoly ($17) blends rum, yuzu, and lemongrass basil.
Whistles whetted, we moved to a table at the back of the dining room. Our view stretched across relaxed diners in lively conversation seemingly very much at home. A couple played cards between courses; at another table, a five-year-old’s doodling was abandoned with the arrival of an enormous, melty sundae. At the end of the room, the open kitchen and its satisfying rhythm completed the picture—one that, save for the hairdos, might not have looked so different a century or two ago.
Like many transplants to the region, the English-born de Boer is struck by the Hudson Valley’s seasons. “You feel the intensity here—everywhere else is seasonal-light, but here you get spring whiplash, summer intensity, all-consuming fall, and then, hibernation.” The menu is a dynamic reflection of those natural cycles.
Seasonality is most strongly expressed at the top of the menu. Artichoke mayonnaise ($19), plated like a deconstructed flower, with fluffy mayonnaise, overlying its heart, is delicately cooked and lemoned, so the artichoke fully shines. It’s fun to eat and a bit messy, on-theme with the unfussy atmosphere. Spongy sourdough is served with a luxurious dollop of butter, carved from a small mountain beneath a cloche—greeting all who enter as a foreteller of flavors to come. Leeks vinaigrette and Ardith Mae, an artisanal goat cheese ($25), are served confit-style with coarse mustard in a pool of sweet brown butter vinaigrette. So tender they nearly melted.
Seafood salad with seabeans ($27) is a standout. Squid, shrimp, and mussels are lightly charred, then chilled and tossed with seabeans, celery, and aromatic tarragon, finished with a shower of sumac.
The wine list favors French, Italian, Oregon, and California producers. Expect food-friendly wines—Pinot Noirs, Chenin Blancs, Burgundies—with options in the $55 to over-$100 range, and indulgences north of $500.
Stissing House is a splurge, but portions are generous and the food nourishing. You’ll likely be full with fewer dishes than expected. If I lived nearby, I’d regularly share a couple of small plates with a friend over a glass of wine and call it dinner.
Whatever you order, don’t skip dessert, and according to de Boer, a scoop of vanilla doesn’t count. The season’s strawberry cobbler with chamomile ice cream for two ($39) easily feeds three or four. House-made ice creams ($10 a scoop) are always offered, and the coconut cake ($17)—cut from a 16-inch round—is a staple for good reason. Nearly as light as angel food and topped with whipped coconut cream and toasted flakes, it’s a sweet joy of texture and flavor.
After three years, Clare de Boer’s Stissing House is both established and celebrated—a testament to how vision can thrive through the alchemy of team, community, and place.
Stissing House is open for dinner Thursday through Monday at 5pm.
