Sleepy Hollow, New York, Philipsburg Manor
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Philipsburg Manor in Sleepy Hollow, New York Daniel Mennerich

Sleepy Hollow, New York

This town in New York's Hudson Valley is legendary thanks to one iconic figure. The Headless Horseman is classic Hollywood horror as well as a local legacy — it's even the high school mascot. Here, go antiquing and leaf-peeping or take cemetery tours and spend hours following in the footsteps of the legend.

What We Love

Union Church of Pocantico Hills: The stained glass windows in this church are a very special treat. Commissioned by Nelson A. Rockefeller, they were crafted by two French greats — Marc Chagall and Henri Matisse. The nine Chagall creations are the only cycle of church windows by the artist in the United States. Download the app for a self-guided tour. 

Philipsburg Manor: The Northeast is not typically associated with slave labor, but the curators of this 18th-century historic farm don't deny its roots. The tranquil living-history museum includes a working farm, manor house artifacts, hands-on textile production, and the story of the estate's 23 enslaved workers and their eventual revolution.

Best Known For

Headless Horseman's Haunt: Officially known as the Old Croton Aqueduct Trailway, this path winds past the legendary sites. Follow the trail behind the 17th-century cemetery, across the river where Ichabod Crane spotted the Horseman, and through misty fields where you just might hear horse hooves galloping not too far away (seriously — sections are open for horseback riding).

Kykuit: Get a glimpse into the historic lifestyle of an iconic American family at this onetime home of John D. Rockefeller. Four generations of Rockefellers lived in splendor in this imposing six-story home. Tour the subterranean art galleries full of priceless Picassos, the beautiful terraced gardens, and the Coach Barn with early-model collector cars and horse-drawn coaches.

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Who It's Best For

Colonial History Enthusiasts: The Hudson Valley's history is tied in to the larger story of early America. The bucolic town was once a cultural hub and a hotbed of revolution. It's fascinating — and easy — to tap into the old stories. 

Fans of Things That Go Bump in the Night: No matter which retelling of "The Legend of Sleepy Hollow" you're into — the Washington Irving short story, Tim Burton's 1999 movie, or the many TV movies and shows — the town blends into the fantasy.  

Don't Say We Didn't Warn You

No Downtown: It's a shame and a shocker that such a charming historic town doesn't have a center to explore. All sites are close to one another, but you'll need a car. 

by: Lena Katz
Lena Katz

Lena Katz is a New York-based contributor to ShermansCruise who has also written for Brides.

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