The Best Things to Do in Sleepy Hollow for Halloween
Brace yourselves, spooky season is coming! And what better way to get into the Halloween spirit than to visit the birthplace of eerie legends — Sleepy Hollow! Not only is it my favorite holiday, but it’s also my birthday, and after visiting during this celebratory time I can honestly say that this charming New York town is the perfect destination for anyone looking for a Halloween adventure! From eerie legendary locations and ghost tours to Halloween parades and blazing pumpkins, there’s something for every type of visitor. So hold onto your head because I’m unearthing the best things to do in Sleepy Hollow for Halloween!
Credit: Margaret Fox Photography
Is Sleepy Hollow a real place?
Yes! The village of Sleepy Hollow, located in New York State, is famous for its association with Washington Irving's short story "The Legend of Sleepy Hollow." The name Sleepy Hollow itself actually predates Irving's story and has historical roots in the area.
Originally known as North Tarrytown, the village was renamed Sleepy Hollow in 1996 as a tribute to the timeless tale. The Legend of Sleepy Hollow was written by Washington Irving in 1820, the story revolves around the fictional character Ichabod Crane and his encounter with the Headless Horseman in the mysterious and haunting setting of Sleepy Hollow. He even drew inspiration from the real-life region near the Pocantico River, which runs through the village and contributes to its scenic beauty.
Oddly enough, before Irving's story, the area had been referred to as Sleepy Hollow by locals due to its quiet, picturesque landscape and dense forests. In 1999, Tim Burton’s film adaptation “Sleepy Hollow” starring Johnny Depp and Christina Ricci created a classic Halloween flick that furthered the legendary town’s haunting allure. Today, Sleepy Hollow remains a popular tourist destination, particularly during the Halloween season when it embraces its eerie reputation and celebrates the legend of the Headless Horseman with various events and festivities.
How to get to Sleepy Hollow from New York City
Sleepy Hollow is located about an hour north of New York City. You can easily take a car, train, or bus to get there.
How to get to Sleepy Hollow from NYC by car: If you prefer driving yourself, you can take the Saw Mill River Parkway or the Taconic State Parkway northbound from New York City. Both routes will lead you to Sleepy Hollow.
How to get to Sleepy Hollow from NYC by train: Take the Metro-North Hudson Line from Grand Central Terminal in New York City to the Tarrytown station. From there, Sleepy Hollow is just a short distance away. You can either walk (17 mins) or take a 5-minute drive by taxi or rideshare service to reach your destination.
How to get to Sleepy Hollow from NYC by bus: You can take a bus from the Port Authority Bus Terminal in New York City to Tarrytown, which is the town next to Sleepy Hollow. Several bus companies operate this route, including CoachUSA and Bee-Line. Once you reach Tarrytown, you can use local transportation, taxi, or rideshare to reach Sleepy Hollow from there.
Credit: @rooney
Fun Halloween things to do in Sleepy Hollow
If you love all things Halloween then Sleepy Hollow, NY is one of the best places to visit in October! I’m rounding up the best spooky activities to do for a frightfully fun time!
The Legend of Sleepy Hollow Sculpture
Just at the entrance to Philipsburg Manor lies the Legend of Sleepy Hollow Sculpture; a 4-foot granite slab sculpted by Michael Gressel which depicts Ichabod Crane fleeing from The Headless Horseman on horseback.
Credit: Visit Sleepy Hollow
The Headless Horseman sculpture
The Headless Horseman sculpture is an iconic must-see site when visiting Sleepy Hollow! Located across the street from the Legend of Sleepy Hollow sculpture, in the Route 9 median between Old Dutch Church and Philipsburg Manor restoration, this spectacular 18-foot-tall rust-colored work of art was created by local artist Linda Perlmutter and depicts the famous Ichabod Crane being chased down by the legendary Headless Horseman.
Fun fact: This sculpture is located just a few feet away from the bridge where the Headless Horseman would have hurled his pumpkin head at Ichabod Crane in "The Legend of Sleepy Hollow".
Credit: Visit Sleepy Hollow
The Headless Horseman Bridge
Sadly, the bridge described in Irving’s "The Legend of Sleepy Hollow" does not exist, however, the location (where a newer, more modern bridge stands) has been marked with a plaque. While it’s still cool to visit the site, if you’re looking for an eerie alternative then check out the Old Style Horseman Bridge. It runs through the Sleepy Hollow Cemetery and is a great spot for a spooky photoshoot! I’ve included the location in Google Maps above to help you find this little hidden gem.
Credit: Sarah Nadeau
Sleepy Hollow Cemetery
Sleepy Hollow Cemetery is the final resting place for the legendary Washington Irving, as well as a number of famous names like Elizabeth Arden, Andrew Carnegie, members of the Rockefeller family, and more. You can come here anytime before 4:30pm on your own to visit or you can take a walking tour. They offer a few different types including a classic daytime tour, nighttime lantern tour, and even a murder mystery ghost tour! Get your tickets in advance here.
Credit: Kailey Parks
Old Dutch Reformed Church
Founded in 1685, The Old Dutch Reformed Church and Churchyard are the very same that appear in Washington Irving’s “The Legend of Sleepy Hollow.” This is said to be the haunting grounds of the Headless Horseman, as well as the burial sites of local citizens who inspired his book’s characters such as Katrina Van Tassel, and Brom Bones. You can take a self-guided walking tour here any time before 4:30 pm.
Tarrytown Halloween Parade
The Tarrytown Halloween Parade is an annual tradition that attracts locals and visitors alike. Held in late October, the parade is a vibrant display of creativity, with a mesmerizing array of costumes, imaginative floats, spooky decorations, and lively music. The parade route winds through the picturesque streets of Tarrytown, creating a festive and eerie ambiance that adds to the Halloween spirit. After the parade, the Halloween festivities continue with various activities, including costume contests, pumpkin carving contests, haunted house attractions, and more. Local businesses often get into the spirit of the season, decorating their storefronts and offering Halloween-themed treats and promotions.
Haunted hayrides
The Haunted Hayride is a tradition in the Village of Sleepy Hollow. Enjoy a 30-minute hell-raising hayride through the woods with live scenes including clowns, witches, a cemetery, zombies, and more spooky things that go bump in the night. There’s also a free block party with live music, entertainment, family activities, and vendors!
The Great Jack O’Lantern Blaze
The Great Jack O'Lantern Blaze is my favorite Halloween activity of them all, and the fact that it’s so close to Sleepy Hollow makes it even better! This fun immersive fall festival features thousands of illuminated and intricately carved pumpkins, larger-than-life art installations, synchronized lighting, and a spooky soundtrack to really get you in the mood. From a pumpkin portal to a spinning carousel, The Great Jack O'Lantern Blaze is a must-see experience that captures the spirit of Halloween and the wonder of the fall season!
Credit: @trytoscareme
Whether it’s exploring eerie locations or enjoying a haunted attraction, there are plenty of frightfully fun activities in Sleepy Hollow to choose from — it’s no wonder why people flock here during the spooky season! As a Halloween lover myself, I absolutely adore this legendary town and I know you will too!
