Now might be the best time ever to visit the Hudson Valley—and not just for its iconic fall foliage and cider doughnuts. Sky High Farm, a historic apple-storage warehouse, was recently converted into a contemporary art space to raise awareness on food justice and local agriculture. And Pocketbook Hudson, a luxury hotel, spa, and restaurant, opens this month in a converted 1885 textile mill. James Beard–nominated chefs and bakers like Clare de Boer and Nora Allen, meanwhile, are relocating here from New York City, elevating the already stellar food scene.
“It’s an interesting mix of locals, the artist community, and people from the city,” Jordana Longo, owner of Ipsum gallery and shop in Hudson, says of the area. “This landscape outside the city really captures something else in people, and you get their attention in a different way. It’s like a door opens, mentally, because of the spaciousness of time and physical space in nature.”
The original people of this region were the Lenape and Mahican, living along the river they called Mahicantuck, “the river that flows both ways.” By 1609, Henry Hudson had sailed through and European settlements had begun around the river valley, and over the next few hundred years the region evolved into a major agricultural hub and weekend getaway for New Yorkers.
A note about geography: The Hudson Valley now refers to a wide geographic region, defined as both the east and west sides of the Hudson River, as far south as Yonkers and north to Albany. Here, we’re focusing on the mid-to-upper eastern side of the river, with the town of Hudson as our home base.
It’s an exciting time in these parts, especially for this local, born and raised Upstate New Yorker and current resident of Germantown, which sits on the banks of the Hudson about 100 miles north of NYC. Below are the places I go back to again and again.
Day one: Contemporary art and country orchards in Rhinebeck
Panamanian visual artist, Risseth Yangüez Singh, at the opening of her exhibition at Contra Projects; path at Burger Hill
Photos by Michelle Heimerman
The easiest way to navigate the Hudson Valley is by car, and if you’re starting out in NYC, you won’t regret leaving as early as possible to beat the traffic. Time it right, and within two hours you’ll be pulling into Golden Russet, a low-key, high-comfort general store and café in Rhinebeck. Order the sausage, egg, and cheese, topped off with a hashbrown (trust me). Then drive 10 minutes down the road to Burger Hill for a short, half-mile hike through picture-perfect meadows, with rewarding views of the Catskills and surrounding farmland.
Next, follow the town’s country roads, which are filled with smaller art galleries. The recently opened Contra Projects is a garage-turned gallery space that highlights Latin American and Caribbean artists like Guatemalan photographer Juan Brenner and Panamanian artist Risseth Yanguez Singh, currently showing her multimedia works tackling the idea of collective memory. (Call or text for an appointment before showing up.) Hiding down another driveway is T Space, an art and architecture foundation in the woods that consists of a gallery and archive that offers year-round guided tours by appointment.
Downtown Rhinebeck is ideal for an afternoon stroll. Enjoy a bite from the newly opened Little Goat, a Mediterranean-inspired café, bakery, and pantry, and then stop into Westerlind, a shop for trendy outdoor gear, or Beekman Arms Antique Market & Gallery, housed in the 1776 Beekman Arms, known as America’s oldest continuously operating inn.
Montgomery Place Orchards is a fine stop for a wide range of apples.
Photo by Michelle Heimerman
For a self-guided crash course in advanced apple studies, stop by Montgomery Place Orchards, a farm in operation since the 1800s with a family-run roadside stand now in its 38th season. It grows close to 70 varieties, from the Esopus Spitzenberg to the Allington Pippin.
While you’re on the apple beat, check out Rose Hill, a classic orchard with idyllic views and wild-fermented cider. Then it’s probably time to switch up the fruits. Sip a blackcurrant apéritif—or the new limited-edition Green Tomato apértif—at C. Cassis’s tasting room, a barn with outdoor seating and a well-designed bar with playful stools and a signature blue bathroom. For dinner, reserve a table at Stissing House in nearby Pine Plains, or just get there early enough to get a seat at its rustic-elegant bar. Enjoy a martini and any of its wood-roasted meals, like roasted halibut with white beans and mushrooms, by candlelight.
Day two: Design finds and local menus in Hudson, Germantown, and Tivoli
The Hudson Valley offers a seductive balance of contemporary design, as seen at Available Items chair collection, and nature.
Photos by Michelle Heimerman
Warren Street in Hudson is a vibrant, well-curated, mile-long stretch of restaurants, antique shops, art galleries, and vintage boutiques. And your first stop should be Mel the Bakery for its perfectly flaky croissants—unless you’re in more of a bagel mood, in which case hit Circles. Grab a latte at Wylde and start meandering.
Ipsum, a collection of ceramics, sculpture, and other unique objects, is the shop of Jordana Longo, who also runs nearby arts space Sunfair with architect Sloan Shaffer. “I want to support people making things by hand, and support craft and design,” she says, “because otherwise I fear those things will be lost.” And Hudson, she adds, is just the place to do that—including at Sunfair, an idyllic venue comprising a farm, sculpture garden, and gallery.
“We don’t do any real marketing—so much is word of mouth,” says Longo. “It allows for it to be more intimate and allows curiosity to lead people here.”
Ipsum’s gallery at Sunfair hosts regular gatherings to showcase art exhibitions and allow the community to enjoy the gorgeous grounds.
Photo by Grant Gulla
For lunch, make your way to Otto’s. Centrally located on Germantown’s small main street, it’s where locals pick up last-minute groceries and cyclists take breaks from riding the Empire State Trail. As of October, thanks to a newly installed pizza oven, Otto’s is expanding its hours and menu with Roman-style pies, appetizers, beer, and wine. After, pop across the street to Mary MacGill to browse her jewelry, art books, and clothing.
Continue a few miles south along a picturesque section of Route 9G and you’ll come to Tivoli, where you can buy a coffee from Tivoli General or a pint of halva honeycomb ice cream at Fortunes—or browse the shelves at Available Items, a locally-owned design store and gallery.
A diner from the 1940s was most recently renovated and opened as the Hudson Diner. Its shrimp cocktail is the perfect appetizer.
Photos by Michelle Heimerman
You’ll want to be back in Hudson for dinner, where you’re spoiled for choice: There’s Feast and Floret for a modern Italian meal set in a charming brick building or longtime classic Lil’ Deb’s Oasis offering bright vibes, fun energy, and a tropical menu paired with great natural wines by the glass. A new favorite of mine is Hudson Diner, opened recently in a converted diner space by the team from Mel the Bakery and the Meat Hook, a New York–based butcher recently opened on Warren. It serves up nostalgic favorites—think patty melts with shrimp cocktail and a wedge salad—made from the highest-quality ingredients. For a postdinner drink, head to Hereafter.
Day three: Feel like you’re strolling through paintings in Greater Hudson & Kinderhook
Morning fog over the Rip Van Winkle Bridge and Hudson River with the Catskills in the background as seen from the grounds of historic estate Olana House
Photos by Michelle Heimerman
One of my go-to morning walks is on the grounds at Olana House, a 10-minute drive from Warren Street. The 19th-century estate of Hudson River School painter Frederic Church combines Victorian architecture with a Middle Eastern influence inspired by his travels. Strolling the grounds is like entering some of Church’s landscape paintings—on display inside and viewable with a guided tour.
From there, drive 30 minutes north to the quaint village of Kinderhook. Saturdays are ideal, when the farmers’ market takes over the small town square. Grab coffee and a breakfast sandwich from the Southeast-Asian inspired Morningbird Café, part of a larger 1870s converted textile mill also home to contemporary art gallery September, and OK Pantry, a curated shop with modern home goods. Kinderhook Books and Saisonnier, with a cozy, tavern-like setting, are two more favorite stops for locals.
Jack Shainman Gallery’s Kinderhook outpost, the School
Photo by Michelle Heimerman
A few minutes down the road is yet another old building enjoying a second life: the School, a former high school converted into a 30,000-square-foot outpost of NYC’s Jack Shainman Gallery that is currently showing work from more than two dozen artists. If you’re more into history, try touring the home of America’s eighth president, Martin Van Buren.
The dining room at Klocke Estate; the post-and-beam storage barn where barrels of brandy age
Photos by Michelle Heimerman
For sunset, drive to Klocke Estate, an ambitious earth-to-glass brandy distillery that opened last year on 160 acres of farmland just outside of Hudson. Winding up the hill through the vineyards and orchards feels like you’ve been transported to a European countryside. Grab a spritz made with either the house red or white vermouth, wander the garden, and take in the Catskills views from its elegant bar and dining room. You might want to stay a while, and luckily you can order dinner off the seasonal menu; options range from steak tartare to cavatelli with local veggies and lemon ricotta.
Day four: Rail trails and sculpture parks in Ghent and Chatham
See the sights by biking in and around the Empire State Trail between Germantown and Hudson.
Photo by Michelle Heimerman
One of the best ways to see the region is by bike, with rentals widely available. The 750-mile Empire State Trail runs through Germantown, Tivoli, Hudson, and Kinderhook, so you’ll often see long-distance riders along the roadways. The more leisurely option (and my favorite) is the Harlem Valley Rail Trail, a 26-mile paved path over an abandoned rail bed that will soon be expanded to 46 miles.
For brunch, stop at Ten Barn Farm for the Parmesan eggs and pesto on sourdough, best enjoyed on the back porch. Two minutes down the road is Art Omi, where you can wander the grounds and admire the monumental sculptures dotting the rolling landscape. Before heading home, stop in Chatham, the future site of the anticipated Shaker Museum (coming in 2028). Get a porcelain banana from Still Life or some sage-scented soap from Marton & Davis, two new shops in town, making it a perfect last stop for some worthy souvenirs.
