Explore the Origins of Rip Van Winkle, a Legend of the Catskills

For years, people have speculated over the historical existence of Irving’s mythic figure (shown above in a painting by N.C. Wyeth). Some of the region’s residents even claim Van Winkle as their ancestor.

More than 200 years after Washington Irving’s tale was published, Catskill’s most famous resident still has a presence in the Hudson Valley.

This story originally appeared in our July 2020 issue.

“Rip Van Winkle, Rip Van Winkle, sleep, sleep, sleep.”

So goes the opening refrain of a catchy 1961 doo-wop song by The Devotions, accompanied by the thunderous crash of a bowling ball striking pins, and the high-pitched cackling laughter of the elves Rip met, prior to his 20-year repose.

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Washington Irving’s tale, published over two years (1819-20) in a collection of short stories called the “Sketch Book,” gave the Catskills a new magical, mysterious identity, which is still very much alive today, 200 years later.

“I always find return trips to the Catskills tranquil and peaceful, much the way Rip Van Winkle carried on his life,” says Steve Reich, history professor, James Madison University in Harrisonburg, VA. “I love the end of the story in which all the children of the town gather to hear Rip tell stories of the past. To be respected in old age like Rip, not for what he did, but for what he knows and what he can teach, I find a compelling model.”

Reich’s late father, George, grew up in the hamlet of Leeds, one of three places Rip might have lived before escaping his domineering wife for what started out as a brief sojourn in the woods. Many local residents assume Rip’s home was in Palenville, where the Rip Van Winkle Trail (Route 23A) begins its winding ascent up through Kaaterskill Clove to the mountaintop community of Haines Falls.

Courtesy of Greene County Historical Society

But in his preface to an 1893 edition of the legend, George H. Boughton says the English-named Leeds and nearby village of Catskill both laid claim to Rip as their native son.

“The Leeds folks show various tumble-down tenements in some places, and the remains of weed-covered foundations in other places, to prove their assertions,” he wrote. “Naturally, the Dutch villagers of Catskill scout this claim.”

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Emmy Award-winning CBS News correspondent Steve Hartman feels an extremely close connection to Rip. An Ohio native, his 18th-century Dutch stone home might very well have been the Van Winkle abode.

“Of course I’d heard the story of Rip Van Winkle growing up, but until I bought a house in Catskill, I had no idea I was moving into the man’s bedroom!” Hartman says. “He’s a fictional icon. So I have lots of fictional pride. The best part of the story is the nap. It’s basically Back to the Future without the temperamental DeLorean (time machine).”

 Regardless of his origins, Rip’s fame quickly spread worldwide. Irving’s story was the first of three powerful forces that began drawing people far and wide to Greene County’s northern Catskills, still known today as “The Land of Rip Van Winkle.”

In 1824, one of America’s first grand resorts, the Catskill Mountain House, opened atop a precipice with commanding views of the Hudson Valley below. To get there, guests took a steep, winding stagecoach ride. Part way up, they could stop at the Rip Van Winkle House for a brief respite, and hike to Rip’s Rock where he allegedly slept.

From breweries to bridges, Rip Van Winkle’s name can be traced all over the Hudson Valley. His sleepy story reflects the tranquil landscape of the region. Photo courtesy of Rip Van Winkle Brewing Company

In 1825, American landscape painter Thomas Cole moved to Catskill, and founded the Hudson River School. His beautiful, romanticized images included many sites close to Rip’s fictional slumber, all of which contributed to the area’s allure.

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For the next 150 years scores of businesses, seizing upon Rip’s popularity, used his name to promote wide-ranging enterprises from Rip Van Winkle Motor Lodge (formerly in Catskill) to Rip Van Winkle Country Club (Palenville) and the former Rip’s Retreat, a themed children’s attraction in Haines Falls during the late 1950s and early ’60s, featuring a puppet show and small buildings, each one offering a different craft such as glass-blowing, candle-dipping, and wood-carving.

More recently, Angela’s — a Catskill dining staple for more than 30 years — added a brewing system and changed its name to Rip Van Winkle Brewing Company. In addition, a handsome historical marker touting Rip’s legacy was placed in Haines Falls. “There’s a lot of pride that goes with it,” says Dede Terns-Thorpe, Hunter town historian. “That’s the biggest thing.’

Of course, the area’s largest Rip-related landmark is the impressive, cantilever Rip Van Winkle Bridge, a mile-long span over the Hudson River that opened on July 2, 1935, connecting Greene and Columbia counties. A row of sculpted hedges at the Catskill bridge approach spells out Rip’s full name in large letters.

Photo courtesy of New York State Bridge Authority

In the late 1970s, however, Rip’s sleepy image began taking a back seat to the lively new ILoveNY tourism campaign, which sought to attract younger downstate visitors, in response to stiff competition from recently opened Atlantic City casinos.

“Almost as quickly as Rip Van Winkle burst onto the world scene, he disappeared,” wrote the late Justine L. Hommel. “But the pursuit of Rip Van Winkle has not ended, and possibly never will.”

Hommel was president of the Mountain Top Historical Society, which in 1988, published a reprint of Irving’s story, serving notice “that the Legend lives, to be shared with a whole new generation.”

“On those summer afternoons when the wind blows a certain way and the skies hold the black look of secrets and age-old mysteries, those of us who live in the Catskills remember,” she wrote in an introductory message. “Each clap of thunder resounding through the mountain peaks reminds us of Rip Van Winkle, of his twenty-year sleep, of gnomes and the never-ending game of nine pins.”

Photo courtesy of New York State Bridge Authority

But for all its entertainment value and commercial contributions to Greene County, the story has a much deeper, far-reaching significance for America, true during Irving’s time and even more so now following a coronavirus pandemic that forced people to stop, slow down, and take stock of life’s highest priorities.

Irving wrote: “The great error in Rip’s composition was an insuperable aversion to all kinds of profitable labor. In fact, he declared it was of no use to work on his farm; it was the most pestilent little piece of ground in the whole country.”

But rather than regarding Rip as a lazy, dreamy idler, Boughton believes Rip’s character is Irving’s “protest against the stress and drive, the feverish energy, and over excitement in the wild race against time, for wealth and power and place in the quickly growing communities about him.”

“[It is] a compelling critique of the work ethic…in American culture. Irving suggests that the new republic needs to make room for poets, philosophers, artists, storytellers, and writers.”

— Steve Reich, history professor, James Madison University

Reich, the college professor, wholeheartedly agrees, as he has related in a United States history survey course covering a period from the dawn of the American Revolution to the present. Students read a number of sources by Ben Franklin, who celebrates the work ethic and the potential for hard work to liberate ordinary people from the shackles of bound labor and arbitrary authority.

“Irving’s story, published in 1820, offers a compelling critique of the work ethic and the place of work, or busy-ness in American culture,” Reich says. “Irving suggests that the new republic needs to make room for poets, philosophers, artists, storytellers, essayists, and writers. Remember that Irving himself is a writer and is deeply worried that the new republic, with its singular focus on hard work as practical and productive work, would do nothing to generate and encourage great art and literature.”

rip van winkle
Rip Van Winkle’s likeness can be seen carved into this Hunter Mountain monument. Photo courtesy of Great Northern Catskills of Greene County

“The American Revolution succeeded in liberating Rip Van Winkle from the tyranny of his wife’s petticoat government, just as it liberated the colonies from the tyranny of the British monarchy,” he says. “But it will only be successful if succeeding generations guard against their own internal drift toward new forms and sources of tyranny. Forcing everybody into a strict and narrow definition of labor and profit is likely to become a new source of tyranny.”

So perhaps, following Rip’s 200th anniversary in 2020, there is no better time to revisit and celebrate all he represents and stands for. What better place than a quiet, mountainside glen in the Land of Rip Van Winkle?

Related: Discovery the History of the Hudson Valley’s Irish Alps

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