Sleepy Hollow from New York City


“If ever I should wish for a retreat whither I might steal from the world and its distractions, and dream quietly away the remnant of a troubled life, I know of none more promising than this little valley.”

Washington Irving,

The

Legend of Sleepy Hollow

There are few places so enchanting as the legendary Sleepy Hollow. Lucky for travelers visiting the big city of New York, you can reach this charming town in under an hour by car or by train from Grand Central Station. Sleepy Hollow makes the perfect day trip from New York City, offering historic sights along the mighty Hudson River.

Old Dutch Reformed Church Cemetery

Old Dutch Reformed Church

The 17th Century Old Dutch Reformed Church in town now boasts National Register of Historic Places status. The old stone church is surrounded by a 2.5 acre cemetery. The cemetery is supposedly haunted by the Headless Horseman and is an integral location in The Legend of Sleepy Hollow. Parking is allowed at the adjacent Sleepy Hollow Cemetery, but keep in mind it closes at 4:30PM.

Sleepy Hollow Cemetery

A whopping 90 acres, the Sleepy Hollow Cemetery was founded in 1849. To make the task of exploring the cemetery less daunting, free maps are available to help you in finding all of the sights within the cemetery. You can visit the graves of Washington Irving, Andrew Carnegie, Walter Chrysler, William Rockefeller, and more. If you would prefer a guided tour with an expert, you can book one through viator here!

Headless Horseman Statue

Linda Perlmutter’s steel sculpture depicts the Headless Horseman charging towards Ichabod Crane. It was first put on display in 2006.

Rockefeller State Park Preserve

If you’re looking to experience some awe-inspiring natural beauty on your trip to the Hudson Valley, visit the Rockefeller State Park Preserve. It’s only five minutes out of Sleepy Hollow! The park is open daily from 9 AM - 4:30 PM and the entrance fee is $6 per vehicle. From the parking lot you can take the short trail to Swan Lake. If you fancy a walk around the perimeter of the lake follow Brothers Path trail (BP), the loop is a little more than a mile. You can find a map of the park and trail guides here!

Great Jack O’Lantern Blaze

A truly spectacular and once-in-a-lifetime experience to have in the Hudson Valley is the Great Jack O’Lantern Blaze! Every September to November, Halloween and The Legend of Sleepy Hollow are celebrated in the Lower Hudson Valley by lighting thousands of hand-carved jack o’lanterns at the Van Cortlandt Manor. You can walk the grounds of the manor and admire the illuminated pumpkins by reserving tickets on the official website. Ticket prices start at $24/person. The historic Van Cortlandt Manor in Croton-on-Hudson is a 20 minute drive from Sleepy Hollow or a 35 minute train ride + walk!

Want help planning your dream trip to New York? Get in touch with me here!

Top Hotel Pick

This high-design hotel offers truly the coolest accommodations in Lower Manhattan. The property has a rich history riddled with famous artists over the years (notice the Edgar Allan Poe portrait in the lobby…). Experience the elegance of The Beekman hotel yourself and enjoy the following free perks when you book through me:

  • Upgrade on arrival, subject to availability

  • Daily Breakfast for two guests per bedroom

  • $100 USD equivalent Resort or Hotel credit to be utilized during stay (not combinable, not valid on room rate, no cash value if not redeemed in full)

  • Early Check-In / Late Check-Out, subject to availability

  • Complimentary Wi-Fi

Image courtesy of The Beekman Hotel

Sibley’s Map of Sleepy Hollow

More to Explore

Want help planning your dream trip to New York? Get in touch with me here!

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