A Little 'Too Sleepy' Hollow? Haunts, Hangs, & Happenings in the Headless Horseman's Hometown

The Sleepy Hollow Lighthouse, or Tarrytown Light, keeps watch over the Hudson River

Nestled up in the Hudson Valley, only an hour or so from the hubbub of New York City, is where you’ll find the small village that author Washington Irving once described as “one of the quietest places in the whole world”, where “the occasional whistle of a quail or tapping of a woodpecker is almost the only sound that ever breaks in upon the uniform tranquillity”. Sleepy Hollow, forever immortalized in Irving’s writing, is still a quaint little place to visit these days; whether or not Ichabod Crane would recognize it in its current state is another question.

It’s true that a “drowsy, dreamy influence” still hangs over the land, but the land is now also dotted with beauty shops, laundromats, hair and nail salons, and a raft of pricey condominiums along the riverfront. The town, at least in October, has all of those Halloween flourishes you would expect — heart-stopping, sidewalk-residing animatronics included — but at the risk of sounding trite, I’ve got to ask: is Sleepy Hollow a little too sleepy? In turn, the devil’s advocate inquires: what if it’s just the right amount of sleepy? (Cue the philosopher: what exactly does it mean for a town to be “sleepy”?) Well, my friends, let’s go ahead and get into it.

Sights & Sounds in Sleepy Hollow

Sleepy Hollow, a town with a population of roughly 10,000, is not a big place. And there’s nothing wrong with that — I mean, we love small town U.S.A., am I right? You don’t go there expecting to find what you would in a major metropolis; you go there for the charm, for the mom-and-pop shops, the cute little cafes, and, in the case of Sleepy Hollow in particular, the local folklore.

Before heading there for an extended mid-October weekend, we looked up a few things to do in Ichabod’s old stomping grounds. At the top of the list, without a doubt, was the Sleepy Hollow Cemetery where Irving himself and a few other famous folks (e.g. Andrew Carnegie, William Rockefeller) are enjoying some well-earned eternal rest. Of course, the cemetery, opened in 1849, is also said to be the home of our good friend the Headless Horseman, who roams the grounds at night in search of his missing head. It is for this reason, perhaps, that the cemetery closes its gates to the public every afternoon at 4:30 p.m. and, thereafter, stations security guards at the edges to deter any would-be ghost hunters.

While unsanctioned after-dark adventures at Sleepy Hollow Cemetery are strictly off-limits, there are a plethora of pay-for-play activities, if you will, that you can take part in. Walking tours, especially those of the kerosene lantern-lit variety, are mighty popular with visitors looking for a guided experience (daytime tours are also available for the scaredy cats out there), or you might choose, as we did, to catch the annual dramatic reading titled “An Evening with Edgar Allan Poe” at the chapel inside the cemetery’s north gate, during which author and performer David Neilsen is temporarily possessed by the spirit of the master of the macabre.

In addition to famous grave sites and the like, other draws at the cemetery include the Old Dutch Church and Burying Ground, which also appears in Irving’s “The Legend of Sleepy Hollow”, and the Headless Horseman Bridge. The church and surrounding burial sites, if we’re being politically correct, are not technically part of the cemetery, but they are immediately adjacent to one another and both are old as dirt, so what’s the difference? Well, dating all the way back to 1685, the church is several times the cemetery’s senior, and is the only one of the two that can factually claim to be home to one of the nation’s oldest continuous congregations.

The Headless Horseman Bridge, meantime, is unfortunately less exciting than it sounds. Not only is the bridge much newer than the one described by Irving in his haunting tale, it also crosses the Pocantico River in a different location. The place where the original bridge would have crossed the river, which is outside of the cemetery grounds and marked by a sign on the side of the street, is now part of Broadway/Route 9, the primary paved road that runs through the area.

On the contrary, the present-day bridge is found inside Sleepy Hollow Cemetery, less than half a mile inside the south gate. And although the infamous bridge has been depicted as a covered bridge in popular culture, historians say there is nothing in Irving’s text or historical records that suggest this is true. Accordingly, the Headless Horseman Bridge of the 21st century is not covered either.

But okay, wow, did we just spend a lot of time on Sleepy Hollow Cemetery and cemetery-adjacent ditties or what? I started out by describing this town as maybe a little too sleepy, but there are other things to see and do outside of the graveyard’s gates. One of those other things is Philipsburg Manor, which, okay sorry, is pretty much kitty-corner to the cemetery, but (!) is entirely its own thing.

The final resting place of “The Legend of Sleepy Hollow” author Washington Irving at Sleepy Hollow Cemetery

While the term Philipsburg Manor actually refers to a large colonial outpost that formerly encompassed about 52,000 acres in what is now Westchester County, New York, the Philipsburg Manor we are concerned with here is comprised only of a small plot of land on which you’ll find the Philipsburg Manor House, a water mill, and a trading site. This property, which sits at the place where the Hudson and Pocantico rivers meet, was, regrettably, the heart of the African slave trading operation of one Frederick Philipse. Today, it is a living history museum with various exhibits and hands-on demonstrations recreating life in the 1700s. During spooky season, they also put on Twilight Village at Sleepy Hollow, which involves fortune telling, a night market, and other shenanigans, and Spirits of Sleepy Hollow Country, which is billed as “an extraordinary evening of mystery” featuring local illusionists.

Due to time constraints, we opted to skip Philipsburg Manor altogether — as well as tours of other local historical sites, such as Kykuit, the Rockefeller family estate-turned-museum, and the Armour-Stiner Octagon House, which is apparently the only known fully-domed octagonal residence in existence — instead having our fun little evening with Edgar Allan Poe at the cemetery and bopping about town in both Sleepy Hollow and neighboring Tarrytown (which we’ll get to in just a bit).

Let’s head to “downtown” Sleepy Hollow for a moment though, shall we? This is where we (finally) circle back to that whole sleepiness debate, which is born out of the fact that there just isn’t much going on in the area around the town’s main drag, Beekman Avenue.

There are some stores, such as Sleepy Hollow Bookshop and The Horseman’s Shop, and a handful of restaurants/bars, including Beekman Ale House and Bridge View Tavern, but those kinds of places are easily outnumbered by the beauty shops, laundromats, and hair and nail salons we were talking about off the top. The dearth of places to grab a bite to eat or gulp down an adult beverage was made even more apparent as we witnessed people waiting in line outside those restaurants and bars early in the evening. How does a town like Sleepy Hollow, which counts, I’d imagine, on raking in thousands of dollars from Headless Horseman-crazed tourists (such as ourselves), not have more food and drink options? ‘Tis puzzling to say the least.

But perhaps Sleepy Hollow is just playing its role, being the sleepier counterpart of the two-headed Hudson Valley monster that also includes a little place called Tarrytown immediately to the south.

Tidings from Tarrytown

Our other main hub while visiting New York’s Hudson Valley was Tarrytown, Sleepy Hollow’s slightly larger “sister city”. Described by Irving in “The Legend of Sleepy Hollow” as a “small market town or rural port” that was given its name by “the good housewives of the adjacent country” due to “the inveterate propensity of their husbands to linger about the village tavern on market days”, Tarrytown is a hoppin’ place compared to its northern neighbor. And things were cranked up just a tick more while we were there due to the fact that the Sleepy Hollow International Film Festival was underway at the historic Tarrytown Music Hall.

After learning the film festival would be in town during our stay, we had checked out the schedule and decided the special presentation of “The Adventures of Ichabod and Mr. Toad” on Saturday morning was not to be missed. D23, the official Disney fan club, and Walt Disney Archives Director Rebecca Cline had traveled to Tarrytown for the screening of the 1949 classic, which was marking its 75th anniversary. The leadup to the main event also included a special screening of “Lonesome Ghosts”, a short released in December 1937 in which a gaggle of misbehaving ghosts play pranks on Mickey Mouse, Donald Duck, and Goofy. Afterward, someone was nice enough to forget their VIP pass in the theater, which made for a lovely little souvenir.

Outside the doors of Tarrytown Music Hall, there is (relatively) much more to do and see. Restaurants, bars, coffee shops, and nifty little boutiques abound on Main Street. You can tell right away that the area has a much more lively feel than Sleepy Hollow (and hey, maybe they are meant to compliment each other this way). One thing that is similar to Tarrytown’s sleepier counterpart is that you will sometimes find establishments with lines out the door. The biggest culprit was Coffee Lab Roasters Inc, which sits next door to the music hall. I swear those people are putting crack in the coffee or something because on both Saturday and Sunday mornings, the line just about stretched all the way down the block.

Rather than wait in line for other establishments, we opted to sit down for drinks at Set Back Inn, a cozy, cash-only, kitchen-less tavern located at 33 Main Street. It’s one of those spots that lets you bring in your own food, which is precisely what we did, getting tacos to-go from The Taco Project across the street. Had we desired some other kind of cuisine, we might have gone with Little B’s Burger Bar, Sweet Grass Grill, or perhaps Lefteris Gyro, all of which are right there in the immediate area, as well.

Thousands of hand-carved pumpkins are set up in elaborate displays at The Great Jack O’Lantern Blaze in Croton-on-Hudson

…And a Cameo for Croton-on-Hudson?

Don’t you just love a hyphenated place name? We had no idea we would be swinging up to Croton-on-Hudson, another small village further to the north, but the pull of The Great Jack O’Lantern Blaze was too strong. This walkthrough experience at Van Cortlandt Manor features thousands of hand-carved pumpkins in increasingly elaborate displays, including a museum of pumpkin art with remakes of classics such as “American Gothic” and “The Scream”, a field of sunflower pumpkins, and their own pumpkin-ified version of the Headless Horseman Bridge. One of the cooler displays, in my opinion, is the “infinity path”: a row of jack-o-lanterns on either side of a dark road that appears to stretch on forever into the darkness.

The family-friendly attraction offers both timed and flex tickets, depending on how you want to tackle it. You can also shell out a little more dough for a VIP ticket, which provides access to the Gourd & Goblet Tavern, along with some other extras. Timed tickets give you a 90-minute window for the Blaze, but you can easily see everything in under 45 minutes if you’re more of a speed walker and/or less of a picture-taker.

-LTH