This Postcard-Worthy Riverside Town Is A New York State Gem

Sleeping in an abandoned zoo might not be the New York vacation you envisioned, but that's just one thing you can do upstate in the quaint river town of Catskill. Built less than 10 miles from where the world's oldest forest was discovered (in Cairo, New York), Catskill includes a picturesque village of the same name, and they both share their name with the Catskill Mountains on the western edge of town. The Catskill Game Farm, America's first privately owned zoo (at one time, also its largest), kept its animals here until 2006. Since then, it has converted its giraffe barn into a boutique hotel, and now you can stay there or enjoy some pet-friendly glamping elsewhere on the Old Game Farm's 200-plus acres.

On a fall New York getaway up the Hudson River with American Cruise Lines, Catskill is the first stop after New York City. On the way back, the last stop before returning to NYC is the village of Sleepy Hollow. These two places are appropriate bookends since they served as settings for Washington Irving's early American short stories, "Rip Van Winkle" and "The Legend of Sleepy Hollow." The Catskills were also the setting for "Dirty Dancing," starring Jennifer Grey and Patrick Swayze. Screenwriter Eleanor Bergstein based the fictional Kellerman's Mountain House on Grossinger's Catskill Resort Hotel, which closed the year before the movie's release. The remains of the hotel burned down in 2022, but you can still bunk where the zoo animals did while you explore Catskill.

The heart of Catskill is Main Street, where it feels like the town that time forgot. It's rather fitting given the place's association with Rip Van Winkle, who famously forgot time by drinking himself into a 20-year sleep. Among Main Street's storefronts, you'll see an old vaudeville theater marquee next to an antique shop. Magpie Bookshop sells "nearly new," while CDs, cassette tapes, and vinyl records fill Spike's Record Rack — where Spotify is a distant memory.

From Memorial Day to Labor Day, the half-mile street turns into a trail of colorful fiberglass cats. The summer art event, Cat'n Around Catskill, culminates in a live auction where you can bid to own one of the decorative felines yourself. They call it the "Cat's Meow" because that's just how appealing these kitties are.

Drinking and dining options in Catskill include the appropriately named Rip Van Winkle Brewery, the New York Restaurant (first established in 1913), and Left Bank Ciders, where the taproom serves the hard stuff made with local apples. America's first major art movement, the Hudson River School, sprang up locally, too, at the Thomas Cole National Historic Site. As part of the Hudson River Skywalk, the Rip Van Winkle Bridge will lead you from there to another historic house museum, Olana, designed by Cole's student, Frederic Church. You can also see Cole's landscape paintings come to life nearby in the 260-foot Kaaterskill Falls, but be cautious when visiting this beautiful New York waterfall.

When you're through Cat'n Around Catskill, you can follow the interactive cat map to the town of Cairo. While its fossil forest is closed to the public, it's only around 30 miles from the Gilboa Museum, where fossils from what is now the world's second-oldest forest (after Cairo's) are on display. That's just one possible side trip from Catskill, which could be a good home base for exploring more historical landmarks in the surrounding region. The Circle W Market, a general store founded in 1908, is another place that feels overlooked by time in the enchanted Catskills.

At the end of Main Street in Catskill proper is Dutchman's Landing Park, where boats can usually launch into the Hudson River (though the ramp is under temporary renovation as of this writing). This is where the free summer concert series, Music in the Park, is held. The 2023 concert schedule included a Woodstock music tribute; Catskill is within a 25-mile drive of the legendary 1969 festival's namesake.

In Woodstock, you can hit up Tinker Street, where singer-songwriter Bob Dylan once lived, and where more vinyl records and period-appropriate clothes are sold at the Woodstock Music Shop and Rock City Vintage. The actual festival took place about 60 miles from Woodstock on a dairy farm in Bethel, New York. At the Bethel Woods Center for the Arts, you can immerse yourself in its history via multimedia exhibits, including high-definition concert footage and a psychedelic hippie bus.