A few years ago, I made a list of all the Halloween inspired places I wanted to visit. Salem was first up and we had a great time exploring the town and learning about the history of the Salem witch trials.
This spooky season, we drove to Sleepy Hollow, NY to explore the setting of Washington Irving’s “The Legend of Sleepy Hollow.” Irving’s short story is a favourite read of mine this time of year, so I was eager to see what the town had to offer.
Halloween decor was everywhere, with houses and businesses here really getting into the spirit of the season.
‘The Legend of Sleepy Hollow’ Must Sees
If, like me, you are mainly visiting Sleepy Hollow in October near Halloween because you love The Legend of Sleepy Hollow (book, movie adaptations and/or shows), then here are the sights you’ll want to see!
Headless Horseman Bridge
“If I can but reach that bridge,” thought Ichabod, “I am safe.” ~The Legend of Sleepy Hollow
The famous bridge where Ichabod Crane was unseated by a pumpkin is the most popular destination in Sleepy Hollow that doesn’t exist … at least not in the same location it’s found in “The Legend of Sleepy Hollow.”
That simple wooden bridge that spanned the river in the late 1700s has long since rotted away.
This Headless Horseman Bridge is located in Sleepy Hollow Cemetery.
*Fun Fact: As vehicles cross the bridge at just the right speed, you can hear the hoofbeats of the Headless Horseman’s horse!
The Old Dutch Church & Burying Ground
“Indeed, certain of the most authentic historians of those parts, who have been careful in collecting and collating the floating facts concerning this spectre, allege that the body of the trooper, having been buried in the church-yard, the ghost rides forth to the scene of battle in nightly quest of his head; and that the rushing speed with which he sometimes passes along the Hollow, like a midnight blast, is owing to his being belated, and in a hurry to get back to the church-yard before daybreak.”
~The Legend of Sleepy Hollow
The Old Dutch Church & Burying Ground was founded around 1685.
The church’s 2.5-acre burying ground is said to be the haunt of the Headless Horseman in “The Legend of Sleepy Hollow.” It’s also the resting place of local citizens who are said to have inspired Irving’s characters of Katrina Van Tassel, Brom Bones, and others.
This small cemetery is found adjacent but separate to Sleepy Hollow Cemetery, where Washington Irving’s grave can be found.
Sleepy Hollow Cemetery
The 90-acre cemetery has seen over 45,000 interments, including some famous ones like Washington Irving, Andrew Carnegie, Walter Chrysler, Elizabeth Arden, and William Rockefeller.
You can walk or drive the grounds on your own or book one of the various tours offered both during the day and in the evening.
It’s a beautiful spot to wander around and enjoy the beautiful October colour. Just be respectful, and if driving, be sure you aren’t blocking driveways or parking on graves as you make your way around.
The grounds close at 4:30 p.m.
Location: 540 North Broadway, Sleepy Hollow, NY 10591
Headless Horseman Statue
“Ichabod was horror-struck on perceiving that he was headless! – but his horror was still more increased on observing that the head, which should have rested on his shoulders, was carried before him on the pommel of his saddle!”
~The Legend of Sleepy Hollow
This 18-foot statue of Ichabod Crane being chased by the Headless Horseman was unveiled on Halloween 2006.
It’s located a few feet from where the Horseman would have hurled his pumpkin head at Ichabod.
It’s a popular photo op and the perfect place for catching up on Irving’s famous legend!
362 North Broadway, Sleepy Hollow, NY 10591
The Legend of Sleepy Hollow Sculpture
Located across the street from the statue by the entrance to Philipsburg Manor, you’ll find The Legend of Sleepy Hollow Sculpture, which depicts Ichabod Crane fleeing for his life from the Headless Horseman.
The sculpture was presented in 1974 to the village of North Tarrytown.
The village changed its name to Sleepy Hollow in 1997.
Location: Philipsburg Manor, 381 North Broadway, Sleepy Hollow, NY 10591
EVENTS
October in Sleepy Hollow offers something for everyone, from ghost tours to blazing pumpkins, storytelling, gothic mansions, a Halloween parade and, if you’re lucky, a sighting of the Headless Horseman himself!
Irving’s Legend
Head to Irving’s Sunnyside, the author’s picturesque estate nestled along the Hudson River, where a candlelit path takes you down to see master storyteller Jonathan Kruk perform his rendition of Irving’s Legend, a dramatic performance of the classic tale. Live music and an appearance from the Headless Horseman himself make this a spooky, spectacular experience for all!
The performance lasts about an hour and takes place outdoors, so be sure to dress for the weather.
More info and tickets can be found here
Home of the ‘Legend’
During the day, you can also take a spooky tour here on the grounds of Washington Irving’s estate. A special exhibit highlights how the Legend has lived on in popular culture through the centuries since its publication.
Location: 3 W Sunnyside Lane, Irvington, NY 10533
The Great Jack O’Lantern Blaze
The area’s biggest Halloween event features over 7,000 hand-carved pumpkins illuminated against the mysterious backdrop of Van Cortlandt Manor’s 18th-century buildings.
Grab a beer or a hot cider and spend an hour or so making your way through the trail of beautifully carved pumpkins.
Tickets need to be purchased in advance. More info can be found here.
Location: Van Cortlandt Manor, 525 South Riverside Avenue, Croton-on-Hudson, NY 10520
There are lots more tours and events happening throughout the month of October, including the Sleepy Hollow Halloween Parade on the Saturday before Halloween.
For a full list of events click here.
Eating & Drinking
Bridge View Tavern
A charming tavern with a good selection of beers on tap and some unique food options like the North American Elk Burger, the Chipotle Bison Burger, the Wild Boar Chorizo Burger, and the Disco is Dead Fries (wild boar fries).
They also have a beer garden. Menu can be found here.
Location: 226 Beekman Ave, Sleepy Hollow, New York 10591
Captain Lawrence Brewing Company
The Hudson Valley’s largest craft brewery hosts a large brew facility, indoor beer hall, and outdoor beer garden. They offer a variety of beers on tap or you can opt for one of the two tasting flights. They also have food, including numerous pizzas to choose from. I recommend the Honeybear Pie!
They now have two locations. More info can be found here.
Tips
The best time to go is in October. The closer to Halloween, the better!
You’ll also find the best fall colours during the month of October.
Most events have parking included with your ticket.
While exploring the town, there are municipal lots with parking for $1 per hour.
The town is very walkable, so find a spot to park and set off!
Beware of the Headless Horseman and enjoy your time in Sleepy Hollow!
Halloween is my favourite holiday. I love the decorations, Hocus Pocus, carving pumpkins, and most of all – dressing up. It’s a magical holiday, so what better place to celebrate than at one of the most magical places on earth! Disney World is one of my favourite places to visit and I’ve always wanted to celebrate the most wonderful time of the year with the magic of the park. So this year, I headed to Magic Kingdom for Mickey’s Not-So-Scary Halloween Party to celebrate Halloween with Mickey and the gang.
It was a great night at the park with all of Magic Kingdom decorated for Halloween, but one of my very favourite parts was getting to dress up in costume and seeing everyone else dressed up, wandering around this magical place!
Salem may be most widely known as the site of the witchcraft trials of 1692, but this colourful coastal city has a lot more to offer: impressive historic architecture, maritime heritage and a rich history spanning nearly four centuries.
Tales of a Travel Addict 
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