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Sleepy Hollow
It’s Halloween all year long in Sleepy Hollow, made famous by Washington Irving’s terrifying tale of the Headless Horseman. But the village has much more going for it, like gracious neighborhoods lined with Colonials, Tudors, and other traditional homes.
Sleepy Hollow
Like Stepping Back in Time
First, a little bit of trivia: Washington Irving’s “The Legend of Sleepy Hollow” wasn’t actually named for this picturesque village. Although bits of the story are set here, including a memorable scene at the Old Dutch Church, Sleepy Hollow only came into being after locals voted to change the name from North Tarrytown in 1996. The new moniker has attracted an army of Headless Horseman fans. (“It is never not Halloween in Sleepy Hollow,” wrote The New York Times.)
But after visiting this river town, many decided that they wanted to make it their home. Start your own exploration of Sleepy Hollow around the main drag of Beekman Avenue. There are charming homes on the nearby streets, many of them Colonials, Tudors, and other traditional styles on small lots that encourage a neighborly feel. A couple of condo developments have sprung up along the waterfront. They’re a stone’s throw from the Sleepy Hollow Lighthouse, one of the area’s most photographed sights.
Where to Get Your Bearings
About half of Sleepy Hollow’s population is Latino, and many of the eating and drinking establishments reflect this heritage. Stop by Sweet Ambateño, on Cortland Street, for pastries, pies, flan, and other sweet and savory treats.
What Locals Recommend
You step back in time when you cross the wooden bridge that leads to the 16th-century Philipseburg Manor, an open-air museum that tells the story of the region’s once-thriving mill trade. In this gorgeous setting, you learn about the back-breaking work required to harvest rye or make barrels.
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Honest Answers to Your
Sleepy Hollow
FAQs
1. Great neighborhoods. Many people move to Sleepy Hollow because they fall in love with residential enclaves like Webber Park (cottages set behind hedges) and Philipse Manor and Sleepy Hollow Manor (gracious homes with sweeping lawns). 2. A love of the past. If you’re a history buff, Sleepy Hollow is the place for you. In the center of Sleepy Hollow is the 16th-century Philipsburg Manor, an open-air museum that chronicles daily life in the region’s mills. 3. A sense of fun. As one observer wrote, “It is never not Halloween in Sleepy Hollow.” Visitors come from near and far to celebrate the Headless Horseman, and locals are happy to join in the fun.
We wouldn’t call it “sleepy,” but this river town does have a laid-back vibe. That’s except for September and October, when 100,000 visitors — about 10 times the hamlet’s usual population — come to experience some thrills and chills at all the places Washington Irving mentioned in his short story.
When it comes to refilling your refrigerator, you have just a couple of options in Sleepy Hollow. Luckily, there are some great options in Ossining to the north and Tarrytown to the south. The same goes for hardware stores and other must-haves when you own a house. It does have Phelps Hospital, run by Northwell Health.
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