20 May, 2022, 01:09

Get Your Spooks on this Halloween with Westchester’s Own Headless Horseman

It’s time to break out the spooky decorations and whip up a creative costume because it’s officially Halloween season! While some dread the end of summer, Halloween-lovers are have already unboxed their new fall boots and are brushing up on their pumpkin carving skills to celebrate the beginning of autumn. In Westchester, New York Halloween takes on a life of its own. 

The famous home of Washington Irving’s The Legend of Sleepy Hollow, Westchester, is a cultural relic. A small town located along the Hudson River, modern-day Sleepy Hollow still holds all of its original charm. If you’ve ever wanted to experience a glorified Halloween, this is where to do it. During the month of October, the residents of Sleepy Hollow welcome thousands of visitors looking to bask in the infamous stories of Irving’s chilling Headless Horseman. The town embraces its status as a cultural icon and holds many events and shows that bring Washington Irving’s tales to life. 

Hold Onto Your Heads

One of the most jovial ways to relive the tale of The Legend of Sleepy Hollow is through The Sleepy Hollow Experience. An immersive theatrical show, during the experience you’ll get to meet all the main characters of this eerie tale, including the headless Hessian himself. Enjoy flowing libations at Van Tassel’s harvest party before being led through the book’s most prominent sites, including the Sleepy Hollow Bridge. Performances take place each weekend in October and the first weekend of November at 6:30 and 8:30 pm.

Looking for something a bit more bone-chilling? Head to Philipsburg Manor for the Horseman’s Hollow haunted maze. Transport yourself back to the 18th century when Sleepy Hollow was rampant with spirits of evil and the walking dead. Come across cursed village people who have a bone or two to pick with unknown visitors and try to escape the grips of the headless horseman as you walk past ancient cemeteries, an old tavern, and the Old Dutch Church. 

Kid-Rated Boo’s

If you love Halloween, but being scared isn’t your thing, then head over to Croton-on-Hudson where they hold The Great Jack O’Lantern Blaze. The Blaze showcases over 7,000 hand-carved jack o’ lanterns that illuminate the night sky. Each pumpkin is carefully carved by a team of artisans and range from outlandish cartoon jack o’ lanterns to life-sized dinosaur jack o’ lanterns. See all the creative ways pumpkins can transform during a tour of the Museum of Pumpkin Art. The exhibition shows classic artworks with a squash-inspired twist. Apart from the art show, there’s a Pumpkin Carousel, a Pumpkin Windmill, and even a Pumpkin Planetarium! The Blaze’s pumpkin light shows, music, and artistry will sure to fill your evening with enough pumpkins to last you through the year. 

The Best Way to Spend Halloween

Wondering where to BOO-k your Halloween getaway? Doral Arrowwood is only a 20-minute drive from Sleepy Hollow and Forbes magazine named it the resort the official “Sleepy Hollow Refuge.” Doral Arrowwood is a picturesque retreat in the countryside of Westchester known for its luxurious lodging and delicious dining options. Apart from its relaxing setting, the resort also has two curated packages to celebrate the Halloween season. 

Their Sleepy Hollow Westchester Weekend package and their Blaze Jack O’ Lantern package offer unique ways to spend a spooky weekend. If early check-in, room upgrades, and Halloween-themed cocktails sound like a great way to kick off your vacation, then check out all the Autumn Escape Packages available at Doral Arrowwood.