The abundant natural beauty and generally chill vibe of the Hudson Valley and the Catskills may be why many New Yorkers flock to the area, but you’ll also find plenty of quirky, whimsical, and just plain cool things to do. But you have to know where to look—here, we’ve picked must-visit cultural institutions, natural landscapes, historic sites, and architectural oddities that should be part of any upstate itinerary.
Though the best way to explore the region is via car—you’ll have more freedom to hop from town to town, which is part of the fun—there are public transit options that’ll take you upstate, too. (Pro tip: The sites here are arranged by distance from New York City.) Many Hudson River towns are accessible via Metro-North or Amtrak, and if you’re heading to the Catskills via public transit, buses regularly leave from Port Authority.
What’s not included here? Lodging, food, and small-town itineraries: If you’re looking for hotels in the Hudson Valley and the Catskills, we’ve got you covered. Want to find good grub? Eater NY has guides to the best restaurants in Hyde Park, the Hudson Valley, and the Catskills (including the area near Hunter Mountain). Planning a weekend trip? Check out our guide to five of the best small towns in the region.
Donald M. Kendall Sculpture Gardens
PepsiCo’s world headquarters in Purchase are home to this 168-acre public space, designed by landscape architect Russell Page (known for his lovely gardens at the Frick Collection in NYC) and filled with works by Alexander Calder, Isamu Noguchi, Henry Moore, and other 20th-century artists. While you’re there, spend some time gawking at PepsiCo’s HQ itself, a sprawling seven-building campus designed by modernist master Edward Durrell Stone.
Blue Hill at Stone Barns
“[T]his restaurant, set on a working farm tucked among rolling hills 30 miles north of Manhattan, is the best restaurant in America because it is more than a restaurant. Under the guidance of Dan Barber, its executive chef, co-owner, and chief philosopher, it is an experiment, a laboratory, a learning center, and a model for the future of agriculture.” —Bill Addison, Eater NY
A meal at Blue Hill at Stone Barns in Pocantico Hills, Dan Barber’s wildly acclaimed farm-to-table restaurant, won’t come easy, or cheap; reservations must be booked months in advance, and its tasting menu costs $278 per person (start saving up now). But the experience of dining there—should you be able to finagle it—will be unforgettable. As Addison put it in his review, “The sense of place and time Barber conjures through food is as life-affirming as it is gratifying.”
Industrial designer Russel Wright spent many years turning a granite quarry in the small hamlet of Garrison, New York, into his dream home—a midcentury estate integrated into the landscape that came to be known as Manitoga, an Algonquin word that means “place of great spirit.” The 75-acre site comprises Wright’s main home and studio (designed in collaboration with architect David Leavitt), filled with his functional-but-elegant housewares, along with an expansive landscape that includes winding paths, a quarry pool, and several verdant gardens. It’s open from spring to the end of October, and a special Metro-North deal makes it easier to visit than ever.
Storm King Art Center
You’ll need more than one trip to take in the positively massive collection and grounds of Storm King Art Center, a 500-acre sculpture garden that sits at the foot of its namesake mountain. Its permanent collection is a who’s-who of 20th-century masters, but special exhibits also go deep on individual artists. If you’ve only got a couple of hours, Museum Hill, near the entrance, and the South Fields, which holds monumental works by Richard Serra and Mark di Suvero, are your best bets. Maya Lin’s “Wavefield,” one of three such installations she’s created in the U.S., is another gorgeous piece—and one that will really remind you that you’re not in New York City anymore. (Just be sure to wear comfy shoes; you’ll be doing a lot of walking here.)
Once upon a time, the castle-like structure on Pollepel Island, located just off the banks of the Hudson River near Beacon, was the center of entrepreneur Francis Bannerman’s retail empire. In the 19th century, particularly after the Civil War, he scooped up surplus military supplies and resold them through a popular catalog, keeping the stock in an enormous fort he designed—taking inspiration from Scottish and Moorish architecture—on the remote island.
An explosion in 1920 and a fire in 1969 left the island in ruins, but now, regular tours show off the grounds and what’s left of Bannerman’s estate. Reaching Pollepel Island is half the fun; you can either take a ferry from Beacon, or, if you’re feeling more adventurous (and athletic), you can kayak from Cold Spring.
In 2003, the Dia Foundation transformed an old Nabisco factory in the once-booming industrial town of Beacon into an upstate hub for its collection of modern and contemporary art. Today, it’s one of the most popular destinations in the Hudson Valley, welcoming thousands of visitors each year. Its collection, spread throughout the 240,000-square-foot building, includes one of Louise Bourgeois’s massive spiders, captivating light installations by Dan Flavin, and several of Richard Serra’s enormous Cor-Ten steel sculptures.
Until +Pool becomes a thing, the best way get your feet wet in the Hudson River is in this pool off of the Beacon waterfront. It’s open from July through Labor Day, and takes inspiration from the “floating baths” that popped up along the New York City waterfront in the late 19th century. The current iteration, a 20-foot swimming spot, is a prototype; its founders hope to construct a larger pool that’ll serve as both summer hotspot and conservation conversation starter. It’s one of many excellent swimming spots in the Hudson Valley region where you can take a dip in the summer.
Stormville Airport Antique Show & Flea Market
One of the Hudson Valley’s largest flea markets is located in the tiny hamlet of Stormville, on what was once a bustling airport for the region. Now, more than 600 (!) vendors set up on weekends throughout the spring, summer, and fall, peddling everything from antique furniture to pop-culture memorabilia to vintage clothes. Each year, the market also holds two yard sales when anyone, not just approved vendors, can bring their gently used items to sell—it’s the perfect chance to clear out your storage unit.
Walkway Over the Hudson
Rising 212 feet above the Hudson River, this rail trail, created from the ruins of the Poughkeepsie-Highland Railroad Bridge, offers Instagram-worthy views of the river and its bucolic environs. (Fair warning: It’s windy up there!) It’s just over a mile long, but you won’t want to traverse it too quickly; there’s plenty to see, including historical markers along the way that offer tidbits about the bridge’s history and restoration. Enter on the Poughkeepsie side for access to cute neighborhoods—Union Street is an adorable historic area—or on the Highland side to get right into your sky-high saunter.
Artists (and husband-and-wife) Peter and Toni Ann Wing began building the structure that would become Wing’s Castle in 1970, and 49 years later, they say that the “live-in art project” is still a work in progress. But the public can visit this medieval-inspired, wholly unique building—which the Wings built using mostly reclaimed materials, including stones, stained glass, and tiles—either for a guided tour, or for an overnight visit.
No, it’s not just an architectural oddity; Wing’s Castle is also a bed and breakfast, with a few rooms available for weekenders. True to its name, those include a queen-sized tower room and a dungeon complete with spooky tunnels; there’s also a moat where visitors can swim and a stonehenge with views of the mountains beyond.
Before this cavernous building, located a stone’s throw from the Hudson River, became a performing arts venue, it was a foundry that produced railway wheels, then a glue factory. Its previous owner, Patrick Doyle, gutted it, creating an expansive canvas for all manner of events: concerts (Patti Smith and the National have performed there), film screenings, dance performances, you name it. Many of the events are proudly avant-garde, but Basilica also serves the greater Hudson community with flea markets, talks with local artists, and more.
Hudson River School pioneer Frederic Church took inspiration from the Middle East for Olana, his family’s estate high atop a hill in Hudson. The resulting structure, designed with the help of Central Park architect Calvert Vaux, is a stunning mishmash of Islamic motifs—colorful tile and stenciling, columns, and arched windows—and Western architectural features, like a mansard roof and glazed windows.
The landscape surrounding the home is equally lovely; Olana’s website calls the 250-acre grounds “one of Frederic Church’s great works of art.” Thanks to a major preservation effort in the 1960s, both the home and the grounds are now open for the public to explore on a number of guided tours; but be sure to book early, since they fill up fast.
Mohonk Mountain House
This beloved resort, a Victorian castle-like confection that dates back to 1869, has hosted all manner of notable names—Andrew Carnegie, Theodore Roosevelt, and Bill Clinton are just some of the famous folks who’ve slept there. Today, what draws travelers to Mohonk is its abundance of outdoor activities: You can paddleboat or fish on Mohonk Lake, go hiking or mountain biking, or participate in a nature tour of the surrounding area. If you want to chill out, the spa—with an extensive list of treatments and a heated mineral pool—is also a fantastic option.
And don’t worry, day-trippers; snag a day pass that gives you access to some of those amenities for a fraction of the price.
Widow Jane Mine
Once a functioning mine known for its abundance of natural cement, this subterranean site has lived many lives: Campbell’s Soup harvested mushrooms from it, it was earmarked as a nuclear fallout shelter for the region, and experimental musician Tony Levin recorded an album there. (Atlas Obscura has a more thorough history of the site.)
Now, the mine is operated by the Century House Historical Society, which is dedicated to preserving the history of cement production in the region. It’s open to the public for tours—be sure to wear shoes you don’t mind getting muddy—and for the occasional concert. This year, you can check out Japanese taiko drumming or a gamelan performance in the mine.
Self-taught sculptor Harvey Fite purchased an abandoned bluestone quarry near Saugerties in 1938, and spent the next four decades transforming the raw rocks and granite into a monumental environmental sculpture. Known as Opus 40, the mammoth space is wholly unique, with discrete sculptures (including a 16-foot monolith at the center of the park) placed atop platforms and winding pathways, all of which were hand-carved and placed by Fite himself.
Fite never quite finished the piece—he died in 1976, 37 years after he began work on the quarry—but as his stepson, Jonathan Richards, wrote, the sculpture is “as complete as it would ever have been.” He continued, “It was the product of Fite’s ceaseless vision, and could only have been stopped with his death.”
Mystery Spot Antiques
The name of this antique store in Phoenicia is an Easter egg for history geeks who also love to thrift: Homer and Langley were the first names of the eccentric Collyer brothers, who gained notoriety after being discovered dead in their Harlem brownstone surrounded by mountains of stuff that they’d collected over the years. Thankfully, the Mystery Spot is more orderly, if still devoted to all kinds of random junk—vintage clothes, creepy dolls, old records (there’s a whole vinyl nook!), antique homewares, and more. A visit is always entertaining.
Hunter Mountain scenic skyride
Known as a destination for ski bums and those who love shreddin’ the gnar, Hunter Mountain also boasts plenty of warm-weather activities, including a chairlift that sails to the top of the mountain’s 3,200-foot summit, providing riders with glorious views of the Catskills and the town of Hunter. Once you’ve hit the peak, you can ride back down, or hike to the historic Hunter Mountain fire tower.
There’s no shortage of gorgeous scenery in the Catskills, but Kaaterskill Falls is a cut above—and has the Instagram popularity to prove it. There are a couple of ways to get to the 260-foot, two-tiered waterfall, according to Hike the Hudson Valley: From a parking area on Route 23A, you can do a quick, mile-long hike along the Yellow Trail (look for a trailhead kiosk close to Bastion Falls). Otherwise, a viewing platform above the falls is also accessible (and potentially easier to reach) from Laurel House Road, where there’s more parking and clear directions to the falls. Be sure to read the New York state Department of Environmental Conservation’s rules for accessing the falls before you head out.
The oldest home in upstate New York is a small 1660s stone structure in Coxsackie, built by a Swedish immigrant named Pieter Bronck (who, allegedly, was a member of the family who gave the Bronx its name). These days, it’s part of the larger Greene County Historical Society, which also includes a collection of Victorian barns that offer a glimpse at what life was like in the New York of yore.
Five State Lookout
“On a clear day, the panoramic view from this location encompasses the White Mountains of New Hampshire, the Green Mountains of Vermont, the Berkshire Mountains of Massachusetts, the Helderberg Mountains of New York and the Connecticut Valley.” —Great Northern Catskills
Catskills Scenic Trail
A 26-mile stretch that was once part of the Ulster and Delaware Railroad is now a rail trail that’s utilized by cyclists, pedestrians, and even horseback riders year-round. It passes through several cute small towns (including Hobart, home to a “book village” of six unique indie stores, and Roxbury, where you’ll find the Roxbury Motel’s quirky, kitschy rooms), and is an excellent—and easy!—way to take in the beauty of the region.