A Weekend in Sleepy Hollow, New York

Ashley Chalmers

Senior Contributor

About an hour north of New York City, you’ll find Sleepy Hollow – the perfect little Halloween escape. Nestled in the Hudson Valley and full of colorful trees and charming Victorian-era architecture, this picturesque hamlet is most famously known as the setting for “The Legend of Sleepy Hollow,” a scary short story by local author, Washington Irving. But while Irving might have put Sleepy Hollow on the map, the stunning village on the banks of the Hudson River has much more to offer than a rogue Headless Horseman.

It’s the perfect day trip from midtown

If you’re heading to NYC for a prolonged trip, there’s no need to uproot and relocate yourself to Sleepy Hollow for a proper tour. Thanks to easy train access directly from Grand Central, Sleepy Hollow is a one-hour journey, made even quicker if you stay in midtown. The Andaz 5th Avenue is a six-minute walk to Grand Central Station, and the experience of travelling from the Manhattan landmark is an attraction in and of itself. Don’t forget to grab coffee and a bagel for the ride.

Pay your respects to Washington Irving

Start your tour of Sleepy Hollow with a peaceful stroll through the Sleepy Hollow Cemetery. Originally called the Tarrytown Cemetery, the burial site was renamed in honour of Irving, and now hosts regular walking tours and other Halloween-inspired special events. Along with the gravesite of Washington Irving, visitors can also pay their respects to other New York notables, including members of the esteemed Astor family, cosmetics mogul Elizabeth Arden, and real estate kingpin Harry Helmsley, who’s interred alongside his wife Leona Helmsley, “the Queen of Mean.” 

Tour the Tarrytown Music Hall

Whether you’re a fan of music history or a lover of architecture, the Tarrytown Music Hall is a worthy stop. Built in 1885, the hall has hosted everything from lavish 19th-century balls to the birth of the motion picture to iconic musicians including Miles Davis and Louis Armstrong. These days, it’s said to house more than a few ghosts - and just in time for the scariest season, the hall offers tours from local author and storyteller Jonathan Kruk. According to the Gotham Paranormal Research Society, the Music Hall is rife with paranormal activity… enough to land it on the Haunted History Trail of New York. 

Go apple picking at a nearby farm

If you drive to Sleepy Hollow rather than take the train, there are plenty of local sites just outside of town - and lots of scenic overlooks along the way, perfect for leaf peeping. The Hudson Valley is particularly known for its apple orchards and local farms. Visitors can go apple picking, sit for a farm-fresh meal, or enjoy seasonal treats like spiced apple cider and warm cider donuts. For the full experience, check out Wilkens Fruit & Fir Farm, which features a bakery and a winery, as well as a corn maze and a pumpkin patch along with sprawling apple orchards. 

See Lyndhurst Mansion’s lavish Halloween decor

Located just south of Sleepy Hollow is the Lyndhurst Mansion – the grand, 19th-century estate previously owned by William Paulding Jr., former mayor of NYC, businessman and merchant George Merritt, and the railroad tycoon Jay Gould. Today, the mansion is open for visits, tours, and events, and features an annual calendar full of Halloween-themed festivities. Classic, family-friendly tours allow you to roam the halls, while evening walks are candlelit and a bit on the scary side!

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