GUIDE TO A SPOOKY day trip TO SLEEPY HOLLOW from NYC
If Halloween is your favorite time of year or you grew up obsessed with The Legend of Sleepy Hollow, then this real-life town in the Hudson Valley needs to be on your fall travel list. Located just about an hour north of NYC by train, Sleepy Hollow, New York is where Washington Irving’s iconic ghost story comes to life each October with spooky sites, historic landmarks, and haunted happenings.
Whether you're planning a full weekend road trip or just looking for an easy day trip from New York City, here’s your go-to guide for what to see and do in Sleepy Hollow.
What Is Sleepy Hollow?
Sleepy Hollow is a historic town in the Hudson Valley best known as the setting of The Legend of Sleepy Hollow, written by Washington Irving in 1820. The town leans fully into its ghostly roots, especially in October, when it hosts themed tours, reenactments, and Halloween events that draw visitors from all over.
Top Things to Do in Sleepy Hollow
Visit Sleepy Hollow Cemetery: One of the most iconic places in town, this is where you’ll find the Old Dutch Burying Ground and the reconstructed Headless Horseman Bridge. Washington Irving is also buried here, so it’s a must-stop for fans of the story.
Walk the original Headless Horseman Bridge: Make your way across the historic bridge that inspired one of the most famous chase scenes in literature. It's a quick walk but a fun one to say you've done.
Snap a photo with the Headless Horseman Statue: Located near the center of town, this statue is one of the most popular photo ops in Sleepy Hollow.
Explore Philipsburg Manor: This 18th-century historic site often hosts seasonal events and gives a great glimpse into colonial life in the region.
Stop by the “Welcome to Sleepy Hollow” sign: Because no visit is complete without a photo to prove you made it.
Lunch and drinks at Horsefeathers: This local favorite has cozy tavern vibes and a great fall menu. It's perfect for warming up after a morning of cemetery walking.
Admire Lyndhurst Mansion: Located nearby in Tarrytown, this Gothic Revival mansion is stunning any time of year, but especially moody in the fall.
Tour Washington Irving’s Sunnyside Estate: Take the Legendary Tour of Irving’s historic home. You’ll learn more about the author himself and see where the legend was born.
Visit the Octagon House for “Myths & Mysteries”: This is one of the more unique haunted house tours in the area. The house is stunning and the storytelling is top-notch.
Catch a live reenactment of “Irving’s Legend”: Held at Sunnyside, this theatrical retelling of The Legend of Sleepy Hollow includes live actors, spooky storytelling, and maybe even a surprise visit from the Headless Horseman himself.
Final Tips for Visiting
October weekends can get busy, so book tours and timed tickets in advance
Wear comfortable shoes, especially if you’re doing the cemetery or heritage trail
Bring a jacket or layers, the Hudson Valley can get chilly in the fall
Plan to spend at least a full day here if you want to fit in most of the highlights
