The Village Of Sleepy Hollow: A Heady October Getaway

Ichabod cast a look behind to see if his pursuer should vanish, according to rule, in a flash of fire and brimstone. Just then he saw the goblin rising in his stirrups, and in the very act of hurling his head at him. — Washington Irving, “The Legend of Sleepy Hollow”

It’s the kind of stuff that legends are made of.


Written nearly 200 years ago, Washington Irving’s account of a schoolmaster beheaded by a Hessian ghost continues to enthrall modern-day fans, who flock to the story’s inspiration and namesake to get a firsthand look at the home of the Headless Horseman.

Located 25 miles north of New York City, along the eastern shore of the Hudson River, the quaint village of Sleepy Hollow doesn’t seem to mind the attention.


If anything, it capitalizes on it, coming to life during the autumn months to revel in the spirit of the season and celebrate its macabre legacy with a host of festive events inspired by Irving’s tale, making it the perfect October getaway.

Sunnyside (Up)

Considered America’s first best-selling author, Washington Irving (1783–1859), spent the last 20 years of his life living at “Sunnyside,” a picturesque Dutch farmhouse along the banks of the Hudson.

The home and scenic grounds have been restored to appear as they did in the 1850s, with many of Irving’s original accoutrements on display.


From May to Mid-November, tours of the property are available and serve as the ideal primer and introduction to the New York town.

“Sunnyside: Home of the ‘Legend” ( is a special series of tours held on weekends (and Columbus Day) in October, providing a more in-depth experience and access to unseen artifacts related to Irving’s tale.

It’s an enjoyable way to spend the daylight hours while learning more about the renowned writer who also penned other classics including “Rip Van Winkle.”

The cost of admission is $16 for adults, $12 for students and seniors, and $8 for children ages 3 to 17.

Horseman’s Hollow

Making a cameo in “The Legend of Sleepy Hollow” is Philipsburg Manor (, the site of a once-thriving gristmill.

The historic, 20-acre property has long since been converted into museum with a working mill, manor house and scenic grounds to explore.

Typically the sort of place that kids visit on a school field trip, Philipsburg Manor gets a ghoulish makeover for Halloween, becoming the super scary “Horseman’s Hollow;” a haunted trail with scenes of horror and mayhem.


Not surprisingly, the theme centers around a 1700s town terrorized by a headless horseman (Spoiler: He makes an appearance), with the experience lasting around 25 minutes.

Recommended for adults and kids ages 10 and up, it’s seriously good fun. Considering that the shrieking guests can be heard from the parking lot, the faint-of-heart might want to sit this one out.

Horseman’s Hollow ( is held on weekend nights throughout October and offers a limited number of tickets. The event almost always sells out, so don’t even think about attending unless you’ve purchased them in advance.

Admission is $20 to $25, with optional skip-the-line passes costing an additional $15 per person.

‘Irving’s Legend’

One of the most popular events in Sleepy Hollow is “Irving’s Legend,” a spell-binding performance of Irving’s classic tale by storyteller Jonathan Kruk.

Held in the Old Dutch Church (one of the town’s most prominent landmarks and centerpiece of “The Legend of Sleepy Hollow”), Kruk makes the most of the dark, candle-lit atmosphere, theatrically drawing the audience into a 45-minute odyssey, complete with spooky organ music performed live in the background.

Historic Hudson Valley Presents "Irving's Legend" at The Old Dut

Photo Jennifer Mitchell

The show is dramatic, satiric and thoroughly captivating, which explains why tickets are sold out long before the performances even begin (sorry, there’s always next year), so they, too, need to be purchased online before you go.

Though it’s recommended for kids ages 10 and up, “Irving’s Legend” ( is open to guests of all ages and tickets cost $25 for adults, $20 for children.

Great Jack O’ Lantern Blaze

Roughly 20 minutes away from Sleepy Hollow by car is Blaze (, one of the area’s biggest, seasonal attractions.


Drawing thousands of spectators each year, the event features more than 7,000 jack o’ lanterns displayed at Van Cortlandt Manor, a sprawling, historic property in the village of Croton-On-Hudson.

A genuine splendor, Blaze is a dizzying array of hand-carved pumpkins (mostly real, with some “art” pumpkins added), fashioned into just about anything imaginable.

Especially notable are a fully-functional Pumpkin Carousel, jack o’ lantern Statue of Liberty, walk-through pumpkin planetarium and pumpkin train.


Synchronized lights and special effects, along with an accompanying soundtrack, round out the walking tour, which takes about 45 minutes.

Tickets to Blaze almost always sell out (sensing a theme here?), so get them early or consider staying over at one of three local hotels with Blaze stay-and-play packages.


The Castle Hotel & Spa (, Doubletree Tarrytown (, and Tarrytown House Estate on the Hudson ( all offer special event stays, combining overnight lodging with VIP passes to the jack o’ lantern spectacular, essentially killing two pumpkins with one stone.

Regular admission to Blaze ranges from $22 to $27 for adults and $16 to $20 for kids ages 3 and up. VIP hotel packages vary in price.

Old Dutch Church And Sleepy Hollow Cemetery

It’s not often that a church and cemetery are considered local hotspots, but in Sleepy Hollow the Old Dutch Church and adjacent Sleepy Hollow Cemetery are two of the most popular places in town.

Dating back to the 1600s, the Old Dutch Church sits atop a hill. Irving refers to it several times in “The Legend of Sleepy Hollow” as a favored haunt of the Headless Horseman, subsequently making it a local destination.


Visitors are welcome to tour the well-preserved church during the day and wander the churchyard where local citizens, thought to have inspired some of Irving’s characters, are laid to rest.

Adjacent to the church is the Sleepy Hollow Cemetery, final resting place of Andrew Carnegie, Harry and Leona Helmsley, Walter Chrysler, Elizabeth Arden, William Rockefeller and, you guessed it, Washington Irving.


Guided tours of the cemetery (including day and evening lantern tours) can be booked online (

Many curiosity-seekers visit the cemetery not only to pay homage to Irving, but also to take a selfie on the Headless Horseman Bridge; the place where Ichabod Crane meets his supposed demise.

It’s not the original site. And, according to most experts, it’s not even the right spot geographically (there’s a sign in town that marks the exact spot).


But since it’s inside the cemetery, where Irving places the iconic bridge in the story, and tucked beneath a large canopy of trees with a totally eerie vibe, it fits the bill.

So everyone takes a photo there. Just because.

Around Town

There are plenty of other activities in the area including a Halloween parade in the neighboring village of Tarrytown (, and a murder mystery experience and Halloween mansion tour at Lyndhurst Mansion in Tarrytown (

The village of Sleepy Hollow with its charming restaurants, boutiques and antique shops is a destination in and of itself (


Shops, lampposts and sidewalks are dressed up with all things Halloween, making even a simple stroll down the street feel fun and spirited.


The local firetrucks are painted orange and black, and in a whimsical tribute, they bear the image of the town’s most infamous “resident” — a Hessian ghost rearing up on his mighty black stallion, in search of a new head.

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