“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
Do you love fall foliage, spooky stories, and quaint towns? If so, you will love discovering things to do in Sleepy Hollow, NY. This village in the Hudson Valley is best known for being the setting of author Washington Irving’s short story, The Legend of Sleepy Hollow. It makes an excellent day trip from New York City, especially during the fall.
Sleepy Hollow has fully embraced its claim to fame and goes all out during the spooky season. From visiting the cemetery to the Great Jack O’Lantern Blaze, there are lots of fun seasonal things to do in Sleepy Hollow. You never know…you might just hear the galloping of phantom hooves in the forest!
Getting There from NYC
- By car: Depending on your starting point, the drive from NYC to Sleepy Hollow can take anywhere from an hour to an hour and a half.
- By train: Take the Metro-North Hudson Line from Grand Central Station to the Philipse Manor stop. The main part of town is about a 15-minute walk from the train station.
Getting Around
The village of Sleepy Hollow is pretty walkable. If you drive in, I recommend parking your car in a central location- such as near the Headless Horseman sculpture on Old Broadway or near Barnhart Park.
What is the Legend of Sleepy Hollow?
Washington Irving’s short story, The Legend of Sleepy Hollow, was published in 1820. It takes place in 1790 in the glen of Sleepy Hollow near the Dutch village of Tarrytown, NY.
The story centers around schoolmaster Ichabod Crane, who is deeply superstitious. Ichabod is particularly paranoid about the Headless Horseman, the ghost of a Hessian soldier who died during the Revolutionary War and is said to ride each night in search of his missing head.
One night, Ichabod is chased by a cloaked figure, hit in the head by a pumpkin, and falls from his horse. He is never heard from again. Irving leaves the story open for interpretation- was it the Hessian ghost or was it Ichabod’s romantic rival trying to scare him away?
Fun Fall Things to Do in Sleepy Hollow
Sleepy Hollow is a lovely place to visit at any time of year, but the following Sleepy Hollow activities are best enjoyed during the fall.
Visit the Old Dutch Church and Burying Ground
In his story, the Headless Horseman is supposedly buried in the Sleepy Hollow churchyard. Turns out that ended up being Washington Irving’s final resting place, as well. Visiting the cemetery is one of the most popular fall things to do in Sleepy Hollow.
The cemetery around the Old Dutch Church is rather peaceful to visit during the day. There are many quiet paths to wander. You might see some familiar names from Irving’s story; but other folks buried there include Andrew Carnegie, William Rockefeller, Elizabeth Arden, and Brooke Astor.
There’s also a sculpture known as the Bronze Lady, who is said to rise and wander the cemetery at night. It’s also said that she bestows bad luck if you insult her or sit in her lap.
You can visit the Sleepy Hollow cemetery on your own or take a guided tour.
Find the Headless Horseman’s Bridge(s)
In the legend, the Headless Horseman cannot cross the bridge near the Old Dutch Church. Poor Ichabod is trying to reach the safety of the bridge when he is struck down.
Although any original wooden bridges have since rotted away, you can find several real bridges attached to the Sleepy Hollow legend. The first is a modern bridge that is part of the roadway, but a marker claims it is the spot that Washington Irving described.
The other is a wooden bridge within the Sleepy Hollow cemetery, located about 0.3 miles from the southern gate. It’s a picturesque spot, what with the nearby graves, and seeking it out is a fun fall activity to do in Sleepy Hollow.
Tour Washington Irving’s Sunnyside
While the original bridge in the story may not exist anymore, Washington Irving’s estate still does! His home sits right on the Hudson and is available to tour.
Irving designed Sunnyside with a friend in the 1830s. They incorporated different European architectural details, making it look like a house out of a fairytale. Many of the furnishings, dishes, and books inside belonged to Irving himself, and the home remains well-preserved.
During the fall season, a storyteller performs a rendition of “The Legend” outdoors at the estate, complete with live music.
Marvel at the Great Jack O’Lantern Blaze
One of the best things to do in Sleepy Hollow in October is to experience the Great Jack O’Lantern Blaze. It may make you feel bad about your own pumpkin carving skills, but it’s still worth it.
The Great Jack O’Lantern Blaze isn’t technically in Sleepy Hollow; it’s in nearby Croton-on-Hudson. Every year, the estate at Van Cortlandt Manor is filled with thousands of hand-carved jack o’ lanterns. You’ll wander through scenes made up of pumpkins, accentuated with light and music, and be amazed at the volunteers’ skills.
The Great Jack O’Lantern Blaze is one of the most popular Sleepy Hollow attractions, so make sure to book your tickets in advance.
Walk Around Rockwood Hall
Walking around Rockwood Hall is one of my favorite things to do in Sleepy Hollow at any time of year. However, when the leaves change in the fall, it’s especially beautiful.
Rockwood Hall is part of Rockefeller State Park Preserve, with walking trails along the Hudson River. During the Gilded Age, Rockwood Hall was the home of William Rockefeller (brother of John D. Rockefeller). The mansion is no longer there, but you can see stone walls where it used to sit.
For an easy 3.5-mile loop, park in a free spot off of Kendal Way, and take the trail across the road. Start with the lower path along the river. Then take the upper path which crosses through fields and rows of big, beautiful trees.
Get Spooked at Lyndhurst After Dark
For those who love all things Halloween, visiting Lyndhurst Mansion is one of the best things to do in Sleepy Hollow in October.
You may recognize Lyndhurst Mansion from HBO’s The Gilded Age, where is has been used as a filming location. This beautifully preserved Gothic Revival mansion in Tarrytown is especially fun to explore during spooky season.
During the fall, Lyndhurst Mansion hosts an event called “Lyndhurst After Dark” during which attendees can experience the mansion by candlelight. Performers discuss Victorian Spiritualism, seances, and other superstitions of the era.
Learn About Philipsburg Manor
Another popular house to visit in Sleepy Hollow is Philipsburg Manor. It’s a living history museum comprised of the manor house, grist mill, and barn. Looking across the mill pond, it’s easy to imagine what the place looked like in the 1750s.
However, on a serious note, you will also learn about the lives of the enslaved people who worked there. Still, it’s educational, and the manor now holds events honoring how Dutch, African, and Indigenous cultures have blended over the years.
Stroll Out to the Sleepy Hollow Lighthouse
If you’re in Sleepy Hollow for sunset, I highly recommend taking a stroll to the Sleepy Hollow Lighthouse. There’s a new pedestrian walkway along the Hudson that has views of the lighthouse and the Tappan Zee/Governor Mario M. Cuomo Bridge.
The lighthouse was built in the 1880s but has recently been renovated, with a ribbon-cutting ceremony this year that coincided with the Village of Sleepy Hollow’s 150th Anniversary.
Experience the Tarrytown Halloween Parade
As I said, Sleepy Hollow and Tarrytown go all out for the Halloween season… and that includes a parade, of course! The Tarrytown Halloween Parade takes places each year during the last weekend in October. It’s a fun time for the whole family, with performers, live music, and outdoor dining.
The parade begins at Patriots Park in Tarrytown, which is said to be where Ichabod Crane first saw the Headless Horseman. It then runs from Broadway to Main Street. (Note: It is a busy weekend, and parking will be difficult.)
Places to Eat in Sleepy Hollow
Assuming you’re not a ghost, you’ll need sustenance during your visit to Sleepy Hollow. Here are some of the best/most popular places to eat in Sleepy Hollow (as verified by friends who live there):
- Horseman Bagels: Start your day off right with a homemade bagel and some pumpkin cream cheese (’cause when in Rome, you know?)
- Horsefeathers: While technically in Tarrytown, this literary-themed restaurant fits right in with the Sleepy Hollow history. Make sure to make reservations or get there early, since it’s a popular spot!
- Bridge View Tavern: As the name suggests, this popular tavern sits right on the Hudson, and it too fills up fast, especially in the autumn months.
- J.P. Doyles: My friends and I ended up here when the Bridge View Tavern’s waitlist was too long, and we thoroughly enjoyed all our food and drinks.
Sleepy Hollow truly is the perfect place to get into the Halloween spirit. Whether you’re visiting for the first time, or have been before, I hope you enjoy a fall visit to this legendary village.
Are you still planning your Sleepy Hollow trip? Save this post for later!
Leave a Reply