Road Tripping from New York City to the Catskills: 8 Great Stops

Escape New York City with a road trip to the Catskills region where unique stops include the Rip Van Winkle bridge, Woodstock history, some of the oldest aircrafts in the Western hemisphere and landscapes that inspired an entire artistic movement.

The old cliché – ask seven people the same question and you’ll get seven different answers – certainly held true when I asked to seven lifelong New York friends: What’s the best thing to do in the Catskills? After hearing their choices, I added my own favorite and put together a diverse two-day, four-county, eight-stop escape around the Catskills that begins just 79 miles north of Central Park.

For nearly a century the Catskills lured folks up from New York City with fine outdoor recreation, swanky resorts and headline entertainment. Curiosity may have killed the cat, but cheap airfare killed the Catskills. Even rising stars like Billy Crystal and Jerry Seinfeld, as well as serving as a backdrop for the blockbuster Hollywood hit Dirty Dancing couldn’t keep the crowds coming after the 1980’s.  Many of the great resorts were shuttered while famous stages were silenced. Then it all started coming back.

An area 43 times the size of Manhattan with 35 peaks over 3,500 feet high, where the world’s most famous music festival was held, where art, architecture, history, hiking and quaint towns call in every direction might have gone down for a decade, but it was never out. And as many of my seven friends and family members mentioned, it was really tough just picking one favorite spot.

Hiking Mohonk Preserve

The Over/Under Line

Mountain peak in The Mohonk Preserve at sunrise, Shawangunk Ridge, Ulster County, New York, USA
Mountain peak in The Mohonk Preserve at sunrise, Shawangunk Ridge, Ulster County, New York, USA.

It’s less than two hours from New York City to the Mohonk Preserve but most folks get antsy on the short drive with the rocks and trails calling. Hikers have 70 miles of former carriage trails to stomp on, with loop or out-and-back options, plus a variety of terrain.

The Undercliff-Overcliff trail is a relatively flat five-mile loop that delivers beautiful views of the valleys, cliffs and mountains. But even more so, it offers cameos of rock climbers, as the name implies, from under and over the cliffs. Here is some of the best rock climbing in the Eastern USA, with more than 1,000 routes and five miles of vertical. If you’ve never climbed but want to, there are 10 different registered guide services that will (literally) show you the ropes.

Flying History at Old Rhineback Aerodrome

Look Up

It started with six derelict World War I aircraft and evolved into America’s first flying museum of antique aircraft. Just four miles outside of Rhinebeck, a village with a growing reputation as a wellness center, the Old Rhinebeck Aerodrome has evolved into an eye-popping collection of vintage aircraft, motorcycles and automobiles.

Aficionados and amateurs appreciate the collection showcased in the museum, but the reason this made local’s best-of-the-Catskills list is what happens high in the sky. Look up any Saturday between June and October and you might spy a 1909 Bleriot, the oldest regularly flying plane in the western hemisphere. Maybe you’ll see a perfect replica of Lindbergh’s Spirit of St. Louis, the plane used for the first solo, nonstop transatlantic flight in 1927. You might even sign up for one of the aerodrome’s famed biplane rides. Visit on a Sunday and you’ll witness a World War I dogfight, complete with hero and villain.

Thomas Cole Historic Site & Olana

Outdoor Art

Spring view of Olana, historic home of Frederich Church along the Hudson River.
Spring view of Olana, historic home of Frederich Church along the Hudson River.

I’ll guarantee you will not fall asleep walking across the Rip Van Winkle Bridge, just like Washington Irving’s famous character did. There’s just too much to see at both ends atop this just-under-a-mile pedestrian crossing of the Hudson River. The bridge is part of the Hudson River Skywalk, which runs a full three miles one-way from Frederic Church’s Olana to the Thomas Cole Historic Site.

If you know historic figures Cole and Church your day will be packed from open to close. If you don’t, well, introduce yourself to teacher and student. Thomas Cole was the founder of the influential Hudson River School of Painting and his home and studio still stand in the midst of the landscape that inspired his art. Cole’s student Frederic Church continued the artistic movement, and his lavish estate Olana is also available for tours. This mid-18th Century duo were the leaders of American Romanticism, a movement greatly influenced by the beautiful landscapes of the Hudson Valley.

Hudson-Athens Lighthouse

There is a Light that Never Goes Out

Hudson-Athens Lighthouse
Hudson-Athens Lighthouse.

Between the village of Athens and the city of Hudson, in the middle of the Hudson River, the beautiful red-brick and granite Hudson-Athens Lighthouse beckons visitors while still serving as an active navigation aid. Its unique shape and Second Empire design adds to its appeal while protecting it from ice floes and river debris.

The lighthouse tour season is short but a guided walk through the eight-room, 146-year-old mid-river marvel makes for a fabulous flashback to a lifestyle gone by. For a return to the present, venture into downtown Hudson where some of the swankiest restaurants, pubs and boutique hotels give the place a bit of a small-town Brooklyn-up-the-Hudson feel.

Table to Farm Foodie Tours

The Fat of the Land

All writers appreciate twists on words and that is what made Table to Farm Tours pop off the “things to do” list for me. Tours introduce you to distillers and farmers throughout the Catskills and Hudson Valley and two tours in particular stand above the rest.

The Sweet and Savory Schoharie Valley tour is about the food, drink and natural beauty of this northern flank of the Catskills. The zealousness of all the local farmers is evident at all stops, including visits to a cidery, creamery, livestock farm, maple syrup farm and a beautiful waterfall. The half-day Delicious Delaware County tour allows you to see and then sample an array of delicious creations from apples to kimchee and cheese to maple syrup, before finishing with a fancy cocktail at the local distillery. Both tours are a great way to taste the best of the Catskills cuisine.

Skiing Hunter Mountain

The Mountain that has it All

Even though I asked all seven friends for the single best thing to do in the Catskills, five of the seven couldn’t resist listing more than one. It seems Hunter Mountain is synonymous with great Catskills spots as four of the seven mentioned this year-round resort that fully utilizes all of the area’s assets.

Skiing is certainly what put Hunter Mountain on the winter adventurer’s map, but it’s the continent’s highest, fastest and longest zipline canopy tour that become a social media sensation. At New York Zipline Adventure Tours at Hunter Mountain, you can soar 60 stories above the ground at over 50 miles per hour, actually crisscrossing other ziplines as you literally fly peak to peak. But you don’t have to go that high, or that fast if you’re someone who prefers to stay closer to ground. There are also some lower-intensity ziplines for the faint at heart.

Museum at Bethel Woods Woodstock History

The Farm in Belthel

Every generation – even those that arrived in the world decades after the big bash at Max Yasgur’s farm – seems to know something about Woodstock. What visitors to the Museum at Bethel Woods soon learn is exactly how much they didn’t know about the most famous arts and music festival of all-time.

Those who were there in 1969 love to say: “if you weren’t there you won’t understand.” While immersive musical and multi-media exhibit displays, plus events and performances are not the same as spending three days on a 600-acre farm with 400,000 of your best friends, it sure gives you a great feel of what times were like during the 72 hours that many say were a “nightcap to the Sixties.”

Woodstock Byrdcliffe Guild

The Town that Got the Credit

Because Woodstock Ventures was the investment group backing the festival, the nearby town of the same name is often mistaken for hosting the epic event. It didn’t. But it did get something that locals call a must-see in the Catskills – the Woodstock Byrdcliffe Guild.

Sitting atop 250 acres, the USA’s oldest operating arts and crafts colony is a stunning setting for exhibitions, performances, classes and workshops – all open to the public. The classes range from ceramics, jewelry and metalworks to weaving, plant growing and writing. Speakers and musicians fill the auditorium (many call it the finest performance venue in the area). Even if your timing isn’t right for a class or an event, a visit to the shop is a worthy diversion. Here, unique creations from established and emerging artists will treat your eyes and challenge your mind.


The Catskills are a place where Mother Nature shows her handiwork and Father Time allows you to slow down and enjoy the ride. There is no shortage of art or activity. It has places to run and places to hide. All offer an easy escape from New York City with a full spectrum of possibilities. And as seven friends shared, it is a place with no shortage of best things to do.

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