Things to Do in Sleepy Hollow During Spooky Season, According to a Local

During the month of October, there is no shortage of spooky activities to partake in for families and grownups alike—but you'll have to nab tickets for them ahead of time.

Philipsburg Manor, a sprawling 18th century milling complex, is at the heart of many of them, including Twilight Village, an immersive experience that takes you back in time with storytellers, live performers and, of course, a visit from the Headless Horseman himself. The experience runs every weekend in October and timed entry tickets must be purchased in advance (they're $25 for children over 2 and $30 for adults).

For the true crime lovers out there, this year brings a new adventure in the Headless Horseman Files, an interactive “whodunit” walking tour that lets you attempt to solve the mystery of what really happened to Ichabod Crane. The 45-minute guided experience runs Fridays in October from 12 to 4:15 p.m. and Saturdays to Mondays from 11 a.m. to 4:15 p.m—tickets are $25 for kids, $30 for adults.

And if you’re hoping to spot some specters, you’ll want to snag a seat at the spectacle that is The Spirits of Sleepy Hollow Country, a spellbinding show that melds magic and illusion. Performances take place Fridays through Mondays in October, and tickets start at $65.

While it’s not located in Sleepy Hollow proper, the Great Jack O’Lantern Blaze at Van Cortlandt Manor in Croton-on-Hudson is just a stone’s throw away, and, speaking from experience, is more than worth the roughly 20 minute drive. A grand, glowing display of more than 7,000 jack o’ lanterns awaits, all artfully hand-carved and truly dazzling. Plus, it’s a no-scares event that’s great for the kiddos. 

The pumpkin-packed event runs through November 16, and tickets start at $24 (children 2 and under get in for free, though!).

I consider myself a bit of a cemetery connoisseur—I hit the local haunt, so to speak, in every new city I visit. So you can take my word for it when I say that Sleepy Hollow Cemetery is one of the greats. Don’t think of it as morbid; consider it more of a living (well, not-so-living) museum of sorts. After all, not only is it home to the Old Dutch Church and Headless Horseman Bridge, two sites featured in Washington Irving’s original tale that put the town on the map, but it’s also the final resting place of Irving himself, so you can stop by and thank him for the frights.

The grounds are seriously stunning, though, and perfect for a stroll on a crisp autumn afternoon. If you care to delve a little deeper into some spirited history, you can purchase a self-guided audio tour ($10; $8) available through an app (which also purports to detect nearby supernatural activity).

But that’s not the only grand manse in the area. You can also explore Kykuit, the home built for none other than John D. Rockefeller, Standard Oil tycoon and, formerly, the richest man in America. The lavish landmark also offers public tours of its opulent, art-filled interiors and glorious gardens through November.

There are various tour options available, though I'd recommend the Classic Tour, which runs for about two hours and takes you through the main floor of the house, its art galleries, inner garden and golf room, with tickets priced at $55 for adults, $44 for young adults (ages 18 to 25) and $20 for children (ages 5 to 17). FYI, no children under 5 are permitted.

Though I’ll usually do a day trip (considering just how close the area is to the city), I’ve scouted a few accommodations for those looking to stay around town. First, there’s the rustic Sleepy Hollow Hotel located just steps away from the Hudson riverfront. The rooms are pretty basic, but it boasts a huge, vaulted lobby dotted with stone fireplaces, an on-site restaurant and an indoor pool.

Seeking a slightly more luxurious stay? Tarrytown House Estate is the hotel of your Gilded Age dreams (ICYMI, lots of industry tycoons nested in the lower Hudson Valley in the 1800s). The historic home-turned-inn certainly feels more upscale—old world elegance meets modern comfort. It’s especially notable for being home to Goosefeather (not to be confused with Horsefeathers), the critically acclaimed Cantonese eatery from celebrity chef Dale Talde. If Manhattanites make the trip just for a meal here, you know it’s gotta be good.