Secrets of Tannersville: Rip Van Winkle, Hidden Dutchmen & A Village Worth Wandering
Welcome to the Land of Rip Van Winkle
It’s easy to understand why Washington Irving set his legendary story in the Catskills. With their swirling fog, sudden cliffs, and ancient forests, the mountains around Tannersville feel full of secrets ... and surprises.
First published in 1819, Rip Van Winkle tells the tale of a man who wanders off into the mountains with his dog, Wolf, and encounters a mysterious group of Dutchmen playing ninepins. After drinking their liquor, Rip falls into a deep sleep, and wakes up 20 years later to a changed world (he slept through the American Revolution!).
Though Irving never names Tannersville directly, the village sits just below the same peaks Rip climbed: Round Top, North Mountain, and Kaaterskill High Peak. If you’ve hiked these trails, you know they still feel timeless.


Find the Hidden Dutchmen of Tannersville
To honor that odd little crew of bowlers from Rip’s tale, local artists and businesses created a village-wide scavenger hunt. Nine tiny painted Dutchmen are scattered across Main Street; some are easy to spot, others are tucked away in windowsills, under eaves, or above shop signs.
There’s no official prize, just the joy of spotting them, and a great way to slow down and explore the village on foot.
Want help getting started? We’ve got a printable PDF to guide your hunt. Download it [here].
Before You Explore
Whether you’re planning a hike or diving into local lore, Camp Catskill is a good place to start. Stop in for maps, gear, and tips on where to find the best views — or maybe a Dutchman or two.
See you in the Land of Rip Van Winkle.
* For more information about the history of the Catskills and Rip Van Winkle, visit the Mountain Top Historical Society at mths.org