Philipsburg Manor in Sleepy Hollow, New York
Philipsburg Manor in Sleepy Hollow, New York / Daniel Mennerich
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Sleepy Hollow, New York
Port
Deal Expert / Travel Blogger

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.

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. 

Lena Katz
Deal Expert / Travel Blogger