All The Reasons Why Halloween Lovers Should Visit Sleepy Hollow This Fall

sleepy hollow

Flickr CC/Gary Lerude

Everyone knows the legend of the Headless Horseman, but did you know you can visit the town that he supposedly haunted? It’s true — you can spend a weekend or a day exploring the town of Sleepy Hollow in the Hudson Valley of New York.

It’s reachable by train from New York City, a 60-or 90-minute ride from Grand Central Station, and you can have your fill of Halloween fun here in the fall.

Get Scared

Sleepy Hollow is packed to the brim with spooky stuff, from the inspiration for the setting of Washington Irving’s famed “The Legend of Sleepy Hollow” to the eerie graveyard where the author is buried.

Washington Irving’s Sunnyside Estate is where the author dreamed up the idea for the Headless Horseman, so if you’re interested in the macabre story, you have to visit. Irving is buried in the Sleepy Hollow Cemetery, where Andrew Carnegie and William Rockefeller were also laid to rest. At night, there’s a lantern tour through the cemetery with retellings of classic area folklore and ghost stories. In Irving’s legend, the Old Dutch Church and Old Dutch Burying Ground is where the Headless Horseman lurked. It’s right next to the Sleepy Hollow Cemetary, so you can visit both in one go.

There’s also Lyndhurst Mansion, a Gothic Revival style home. That means the architecture resembles the old-school mansions from the 12th to 16th centuries. Think European cathedrals like the Notre Dame in Paris. The Kykuit Rockefeller Estate is another example of gorgeous but slightly creepy architecture in the area, as well as the colonial Philipsburg Manor.

sleepy hollow

Flickr CC/Tim Evanson

Get Food

For something fresh to bring on a Halloween picnic, stop by the Sleepy Hollow Farmers Market for artisan baked goods, cheeses and seasonal fruits and vegetables.

For a sit-down meal, head to Sweet Grass Grill. It’s farm-to-table food, including a wild mushroom and porcini fettuccini and miso-glazed salmon. But if you want the reigning local royal of farm-to-table cooking, check out Blue Hill at Stone Barns. It’s a big ol’ splurge if you eat in the restaurant (reservations required), but there’s also a cafe option where you can munch on small plates and snacks by the same ace team behind the fancy dining room.

sleepy hollow

Flickr CC/City Foodsters

Get Drinks

Looking for a drink after all that supernatural searching around town? Whether you need to settle your nerves after seeing a specter or just take a load off, you’ve got two big choices for craft beer in Sleepy Hollow. Bridge View Tavern is close to the center of town and offers beers and ciders, as well as a special beer garden menu. The Oath is in neighboring Tarrytown and also has an extensive beer list that will satisfy the pickiest of beer drinkers.


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