Travel Guide: Sleepy Hollow

Travel Guide: Sleepy Hollow

This weekend marked my fifth fall adventure to Sleepy Hollow, aka North Tarrytown in the Hudson Valley of New York. When I lived in Ohio, I remember only dreaming of a trip to the village made famous by Washington Irving, so as soon as I moved to the city I made it my number one fall priority. It was better than I even expected, and I’ve gone every year that I’ve lived here—except 2016, but I went to Salem that year, so that’s a valid excuse.

There are plenty of non-Halloween related activities to do in and around Sleepy Hollow, but to get the full effect it’s best to visit in October (keep in mind that while it’s not as crowded as Salem, ticketed events sell out very quickly so get them as soon as they go on sale in early September from Historic Hudson Valley).



My favorite part about Sleepy Hollow is that you don’t need a car to get there. It’s under an hour by Metro North from Grand Central to the Tarrytown station, and trains run frequently. Once you’re in Tarrytown you can use a car service like Uber or Lyft to get you into town or to the sites nearby, but most things are within walking distance of the train station. We did have an issue once with spotty cell service when we were relying on Uber to get us back into town after visiting Union Church, but after renting a Zip Car one year (and dealing with the traffic on the one, two-lane road that runs through town), I’m solidly team public transit.


There is no doubt that Irving’s short story, The Legend of Sleepy Hollow is the reason why the area is a popular October destination. In fact, North Tarrytown officially changed their name in 1996 to Sleepy Hollow, the traditional name for the area. Purchased by Irving in 1835, Sunnyside is a National Historic Landmark and a museum containing a large collection of Irving's original furnishings and personal items.

Located in the nearby town of Irvington, the house is open May-November and tours are led by guides in period costume. In the fall you can also “create Halloween-themed art activities, explore the grounds on a literature-themed scavenger hunt, play historic games, pose for a spooky photo op, and take in a shadow puppet performance.”


Kykuit was the 40-room home of four generations Rockefellers, beginning with John D. Rockefeller, founder of Standard Oil and noted philanthropist. The stone mansion is situated on the highest point in Pocantico Hills, overlooking the Hudson River and on a clear day you can see the New York City skyline. In addition to the house, the property includes beautiful gardens and an impressive art collection.

If you want to see something specific make sure you choose the right tour—I’ve been twice, and I would definitely recommend making time for the grand or classic tours. Although Kykuit is located outside of the village, tours originate from the visitor center at Philipsburg Manor (across from the cemetery) and a shuttle bus takes you to and from the estate.

Lyndhurst, a Gothic Revival mansion, was designed in 1838 and had five different owners from three different prominent families before it became part of the National Historic Trust for Preservation in 1961. The mansion is furnished with original furniture/décor from all five owners so the inside is just as interesting and historic as the outside (and, if I’m picking favorites, it’s my favorite of the historic homes in the area). The 67-acre grounds include the bones of the nation's first steel-framed conservatory, a stand-alone bowling alley, a rose garden and a children's playhouse all with sweeping views of the Hudson River.

Open for tours March-December, the mansion and grounds were decked out for Halloween when we visited. Even without the extra help, Lyndhurst is spooky enough on its own and has appeared in numerous movies and TV shows including two star turns as the Collinwood Mansion in the 70’s films House of Dark Shadows and Night of Dark Shadows.


The church itself, built in 1921 by John D. Rockefeller, Jr., is pretty standard but the church’s rose window was the last work completed by Henri Matisse before his death in 1954. Nine other stained glass windows were created by Marc Chagall, who didn’t start designing in glass until he was nearly 70 years old. Other Chagall windows can be found around the world and in the UN building in New York.

The church is open from April-December with varying hours depending on the worship schedule, there is a suggested donation if you visit just to see the windows, and photography is not allowed inside. The church isn’t really within walking distance from the village (and it’s up in the hills), but it’s just a short car ride away (again, beware the spotty cell service).


The Great Jack O’Lantern Blaze is what put this area on my radar eight hours west in Ohio. Held every year at the historic Van Cortlandt Manor in Croton-on-Hudson (not exactly walkable from town, but just a short car ride north), the Blaze seemingly gets bigger and more popular every year. Tickets for weekends close to Halloween sell out very quickly, but it’s worth some advance planning to see more than 7,000 hand-carved and illuminated jack o’ lanterns (spoiler alert: they’re mostly fake, but there are some real pumpkins mixed in). I’ve been to the Blaze twice and can attest that, while there are some repeats from year to year, enough changes that you could go again every year and still be thrilled.


Billed as “Sleepy Hollow’s premiere haunted attraction,” Horseman’s Hollow is like corn maze and a haunted house combined. Set outside on the grounds of Philipsburg Manor, guests—if you dare!—walk along a haunted trail populated by all types of spooky scenes and creepy people. I’ve never been a huge fan of paying to be frightened, but I’ve gone through Horseman’s Hollow twice and I think I finally understand the appeal of these attractions. Skulls, spiderwebs and mannequin parts don’t actually scare me—have you seen my apartment?—but there is a strange sort of thrill in watching your friends get (harmlessly) startled and in surrendering to it all yourself.


Speaking of tickets selling quickly, this is the first year I was actually able to secure tickets to Irving’s Legend, a dramatic retelling of the famous Legend. Held at the Old Dutch Church (located within Sleepy Hollow Cemetery), the story is told by one man, accompanied by one musician. It’s low-tech, old-fashioned storytelling at its best and it’s the perfect way to get acquainted (or reacquainted) with Irving’s spooky tale.

This was a new event for the 2018 season, an original silent film starring Bill Irwin accompanied by live musicians and special effects provided by a Foley artist. Inspired by Washington Irving’s The Adventure of the Mysterious Picture, the film was shot on location at Van Cortlandt Manor. I’ve never seen a silent film before, but I was just as interested in watching the Foley artist produce sound effects for every character as I was in watching the actual movie.


Details on when to secure tickets to the Village of Sleepy Hollow’s Haunted Hayride are a little murky but this year I just kept checking the website and eventually was able to buy tickets. Tickets go on sale “sometime in September” only through the villages’s website, and the Hayride is for two nights only—the Friday and Saturday before Halloween. It started raining just as we were settling into the bed of hay (pulled by a pickup truck), and it wasn’t nearly as scary as walking through Horseman’s Hollow—but we felt about as far away from New York City as we could get, while still being a short train ride away.


One of my favorite cemeteries (and I’ve seen…a few), Sleepy Hollow Cemetery is home to a number of famous residents, including a Rockefeller, a Chrysler, the Helmsleys, Andrew Carnegie, Elizabeth Arden and, of course, Washington Irving himself. Formally opened in 1849, the cemetery is 85 acres and has over 40,000 in-ground interments. They offer day and night walking tours but keep in mind if you’d like to explore on your own that the grounds close promptly at 4:30 pm every day.

Located on Main Street, just up the hill from the Tarrytown train station, Muddy Water is a great place to stop and fuel up before beginning your fall adventure day. There is plenty of cozy seating, the coffee was good, the blueberry scone was delicious (have them heat it up) and my order came to a very festive total of $6.66.


This section is short because I really only ever eat dinner or lunch at one place in Sleepy Hollow—Horesefeathers—and I love it so much that I can’t bring myself to try anywhere else. Ok, so we did make the mistake of eating at The Huddle once and it was terrible, so learn from us (here is the Yelp review by my friend Alisha, detailing our issues) and stick with Horsefeathers.

Family owned since 1981, Horsefeathers is exactly the kind of dark, wood-paneled bar that you’d expect to find in the area, and I dream about their Knickerbocker burger (paired with a seasonal cider) all year long. As if that wasn’t enough of an endorsement, they’re usually playing a Halloween movie at the bar (one year it was Casper) and they have ancient boxes of Trivial Pursuit cards on every table (Sample Q: Which country pulled out of NATO in 1967?), so at least stop in for a drink.

Want more? See all of my Sleepy Hollow posts here.

Valley of the Kings

Valley of the Kings

Happy Friday!

Happy Friday!