Halloween Happenings in Westchester

Oct 12, 2019

From blazing pumpkins to headless horsemen, the most spook-tacular events are about to begin…


Get your ghouls and ghosts out of the attic—Halloween is right around the corner! This is my four-year-old’s favorite time of the year and, being in the Rivertowns, I can’t help but be all-in, too. Living here, we’ve got some of the most amazingly spooky events and experiences right in our backyard. Really, though, what would you expect from the area that sparked the most famous spooky story ever, The Legend of Sleepy Hollow?

With Halloween tales like those are buried deep into Westchester culture, it’s no surprise you’ll find thousands of blazing jack o’lanterns, cemetery tours, haunted houses, scary hayrides, costume parades and all the trick-or-treating your family can handle, right here in our borders. And if you’re ready to dive in, you’re in luck—there’s lots going to start now.

Cemetery Tours, Sleepy Hollow

An evening lantern tour through the famous Sleepy Hollow cemetery is the perfect way to get into the Halloween spirit. Creep through windy paths and shadows between tombstones. Visit the resting places of author Washington Irvington—who penned the headless horseman tale—plus a revolutionary war militia captain and other well-known historical figures.

If that sounds like a spooky-good time—and if your kids don’t scare easily—the cemetery also hosts Spooky Story-Telling from Six Feet Under for families with kids aged 7-12. There’s also a Champagne Cocktails With the Dead for adults.

Horseman’s Hollow, Sleepy Hollow

Leave the kids at home and be prepared for a haunted walk through a scary town—a town that’s gone mad at the hands of a headless horseman. While you explore this timeless legend first-hand, be prepared for anything and everything to come your way from vampires and witches to undead soldiers, ghouls and ghosts.

The Great Jack O’Lantern Blaze, Croton-on-Hudson

This is one of the most popular events in Westchester—and with good cause. Grab the kids and stroll through a dark path packed with 7,000 beautifully designed jack o’lanterns that light up the night. All pumpkins are designed by area artisans and come together into huge structures and shapes—this year expect a sea serpent and at least one haunted house.

Haunted Hay Rides

Sleepy Hollow has an annual scary hayride you don’t want to miss. During the ride, you may even catch a glimpse of the headless horseman himself. Before or after the ride, check out the neighborhood block party to mix and mingle with local families.

For kids who want a not-so-scary Halloween experience, check out the free hayrides around the supermarket Stew Leonard in Yonkers. They start on October 1st and are perfect for younger kids—be sure to grab a pumpkin or two on your way out.

Haunted Houses

What’s Halloween without a truly frightening haunted house experience? Rye Playland turns part of their park into a 12,000-square foot haunted house complete with an outdoor cemetery. Come face-to-face with a cast of terrifying characters, all waiting to greet you and usher your family into the spooky scene.

There’s also a must-see haunted house in White Plains. Here, two frightening houses sit on eight acres of land, with visitors winding through a scary walk through the woods and haunted cornfield.

Pumpkin Farms

Picking and carving a pumpkin (or two…) is a must during the Halloween season. And, luckily, there are plenty of places to do just that in and around Westchester.

Muscoot Farms, Katonah

This popular not-for-profit farm has plenty of animals for kids to visit with—that alone attracts families all year long. In October, though, the farm adds in pumpkin-picking weekend complete with hayrides, an old tractor, balloon-making and a food stand.

Stuart’s Farm, Granite Springs

Located in Somers, this family-run farm is the oldest in the county, having first opened its doors in 1828. The farm has a large pumpkin patch and also offers hayrides on weekends.

Wilkens Fruit & Fir Farm, Yorktown Heights

Though open—and very active—all year, this farm opens its pumpkin patch on October 1st, bringing even more visitors. Don’t miss the onsite corn maze where kids can run and play. After, refuel with baked goods—their famous apple cider donuts are delicious. For parents, hop into the winery before calling it a day. You deserve it.

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