This Mystical Small Town Is A Real-Life Sleepy Hollow & It's A Road Trip From Ontario

It's home to Headless Horsemen and gothic mansions. 🐎🎃

Sleepy Hollow in New York State.
Associate Editor

Sleepy Hollow in New York State.

You may be familiar with the spine-tingling film Sleepy Hollow or the tale that inspired it, but did you know that this little village actually exists?

Sleepy Hollow is a real place located in New York State and it makes for a spooky fall road trip from Ontario. It's about a 6 hour drive from the Niagara Falls border, so you may want to plan a few days to fully immerse yourself in the mystical atmosphere of the town.

The village is home to about 10,000 residents and "offers a unique blend of natural beauty and urban amenities along with world-renowned historic landmarks and modern attributes" according to the Village of Sleepy Hollow.

The town draws thousands of visitors every year and is especially spectacular during the fall when it hosts a variety of Halloween events. Here's what to know if you're planning an autumn escape to Sleepy Hollow.

Where is Sleepy Hollow in real life?

Sleepy Hollow is tucked away in New York State, about 25 miles north of New York City. It sits along the eastern shore of the Hudson River in Westchester County.

If you're travelling there from Ontario, it's about a 6 hour drive from the Niagara Falls border. If you're up for a longer journey you can take a train from Toronto to the adjacent Tarrytown. The trip will take around 12 hours and 30 minutes and includes one transfer.

What is the story 'Sleepy Hollow' about?

If the name "Sleepy Hollow" sounds familiar, it's likely because you've come across Tim Burton's popular film or the original story at some point. The original tale comes from author Washington Irving, who published the short story The Legend of Sleepy Hollow in The Sketch Book in 1819-20, according to Britannica.

The story revolves around the schoolteacher Ichabod Crane who is confronted with the spine-chilling figure known as the Headless Horseman.

The tale has been adapted for film several times, one of the most notable being Tim Burton's 1999 Sleepy Hollow starring Johnny Depp and Christopher Walken.

According to Uncovering New York, Irving's tale became so popular that "the community of North Tarrytown officially changed its name to Sleepy Hollow in 1996 to embrace its place in the story."

Is Sleepy Hollow NY worth visiting?

If small towns, spooky vibes and tales of the past are your cup of tea, then Sleepy Hollow is worth a road trip. The town has lots of activities and places to explore.

You can take a trip right into the spooky tale of Sleepy Hollow by visiting the Headless Horseman Bridge. According to Visit Sleepy Hollow, the bridge in Irving's story does not exist, at least not in the present time, but you can still see the Cemetery Bridge, which is "rustic enough for a selfie" and located near the place where Ichabod Crane "was unseated by a pumpkin."

One of the "most visited" spots in Sleepy Hollow is the Headless Horseman Statue. The 18-foot tall sculpture depicts Ichabod Crane and the notorious Headless Horseman atop their steeds. During the fall, the base of the statue is decorated with pumpkins and hay bales.

Another destination that was featured in Irving's story is the Old Dutch Church. The church's burying ground is the "the purported haunt of the headless horseman" and visitors are asked to be respectful as the venue is still operational.

Philipsburg Manor is another spot that draws visitors in the area. The "colonial-era farming, milling, and trading centre" was also featured in The Legend of Sleepy Hollow and has been restored to its 1750 appearance.

Aside from attractions, you can enjoy lots of local shops such as Headless Horseman Gifts, which is "home to all things headless" and offers souvenirs like keychains, magnets and hoodies.

Sleepy Hollow Bookshop features more souvenirs like postcards, shirts and tote bags.

Halloween in Sleepy Hollow

Halloween season is the optimal time to visit Sleepy Hollow. The town transforms into a haunting village reminiscent of the one in Irving's chilling tale. You can even see the ghostly Headless Horseman!

Throughout the month of October, there are many festive and eerie activities to take part in, both in the town and the surrounding area.

The Great Jack O'Lantern Blaze is a mystical event to check out. The illuminated trail takes you past more than 7,000 hand-carved pumpkins set along a riverside landscape. You'll see the "mysterious" Van Courtlant Manor lit up with these glowing orange gourds.

The adventure has synchronized lighting and an original soundtrack as well as installations like a "twirling pumpkin Ferris wheel."

If you're feeling brave you can take a tour through the Sleepy Hollow Cemetery. There are several tours offered including Daytime Tours and Evening Lantern Tours. You can learn about Washington Irving, the author of the short story The Legend of Sleepy Hollow, hear spine-tingling tales of murder and more.

You can immerse yourself in the tale of Sleepy Hollow by attending events like the Headless Horseman Ball at Castle Hotel & Spa or the The Legend of Sleepy Hollow outdoor experience at Washington Irving's estate.

Other events include a Haunted Hayride, Sleepy Hollow Street Fair, Glass Pumpkin Patch, and gothic mansion tours.

Was 'Sleepy Hollow' filmed in Sleepy Hollow?

While the village that served as the inspiration for Irving's tale of Sleepy Hollow might seem like the natural choice for Tim Burton's 1999 movie, it was, in fact, filmed in England.

However, Sleepy Hollow has served as the setting for numerous films over the years, including motion pictures dating back to the silent era.

The Headless Horseman was said to be filmed in the area in 1922 and features locations such as the Old Dutch Church. Other films include The Preacher’s Wife, The Thomas Crown Affair, The Family Man, Mona Lisa Smile and more.

Whether you come to glimpse the Headless Horseman or to fill up on spooky vibes, Sleepy Hollow is a mystical fall destination to visit from Ontario.

There are several other U.S. towns and cities with Halloween vibes, including Salem, which was home to the infamous witch trials.

From eerie graveyards to gothic mansions and haunting events, Sleepy Hollow is a go-to spot for Halloween enthusiasts.

Before you get going, check out our Responsible Travel Guide so you can be informed, be safe, be smart, and most of all, be respectful on your adventure.

Madeline Forsyth
Associate Editor
Madeline Forsyth is an Associate Travel Editor for Narcity Media focused on Canadian and global travel and is based in Toronto, Ontario.