The Ultimate Westchester Halloween Bucket List

Every spook-tacular activity you need to try before shuffling off this mortal coil.

When it comes to Halloween, the land of Washington Irving is hard to beat for authentic All Hallows Eve shenanigans. Yes, we’ve got Sleepy Hollow, but there are so many creepy events planned in Westchester that, frankly, if you blink you could miss a terrific opportunity to scare yourself silly.

To help you out, we’ve compiled a handy list of what we think are the absolutely quintessential Westchester Halloween experiences. After all, you only live once, right?

Let’s Get This One Out of the Way

Visit Sleepy Hollow. Listen, you just have to. Can it be a little touristy? Sure. But it’s also the spookiest space this side of Salem during October, and Historic Hudson Valley makes sure you get plenty frights with your historical accuracy. Aside from all the local festivities, we recommend going whole-hog and experiencing Irving’s Legend at Philipsburg Manor. It’s the original tale of the Headless Horseman, enacted like you’ve never seen anywhere else, and it’s open Fridays through Sundays every weekend in October. You can also visit the Lyndhurst Mansion in neighboring Tarrytown, decked out every year to offer visitors tours of “Jay Ghoul’s” resplendent home. Tours are available from September 30 through Halloween, while Jay Ghoul’s House of Curiosities mystery tours run October 19 through 31.

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Dig Up Some Old Friends

Tim Evanson | Flickr

Maybe being surrounded by so many lively people isn’t your idea of a good time. Why not visit some old friends? Like, really old. Decomposing, technically. There’s a host (or horde?) of famous figures and local celebrities just lying around Sleep Hollow Cemetery all the time, just dying for the chance to pick your brain. For Westchester’s Stephen King fans, the Hartsdale Pet Cemetery is also a gorgeous stroll, and a testament to how much Westchester loves its pets. Bonus: It’s like ninety percent guaranteed to not be built on a Native American burial ground!

Shock, Schlock, and Tinseltown Terror

Photo courtesy of Historic Hudson Valley

Who doesn’t love a good scary movie? [Raises own hand.] The Jacob Burns Film Center has an annual tradition of screening a one-night-only Halloween Movie Marathon each year, full of classic slashers and lesser-known knock-outs. Now in it’s fifth year, $55 (or $45 for students and JBFC members) will get you in for Cujo, The Dead Zone (the 1983 Cronenberg version starring Christopher Walken), The Devil’s Doorway from Northern Ireland, Halloween 4: The Return of Michael Myers (soon to be non-canon!), the French-Belgian Revenge, 1973’s Sisters starring Margot Kidder, cult classic Slumber Party Massacre, the Iranian Under the Shadow, Canada’s What Keeps You Alive, and Italian blood-bucket masterpiece zombie 3. This year’s date is October 26. If that seems a bit much for you, don’t worry; us wimps can very happily catch a weekend screening of Día de los Muertos family film The Book of Life on the 20th and 21st.

To harken back to the golden age of Hollywood, also consider the following: This year, the newest attraction at Sleepy Hollow’s Philipsburg Manor is The Unsilent Picture. It’s a brand-new silent film in glorious black-and-white, starring Bill Irwin and featuring live music and special effects. The film recounts Washington Irving’s “The Adventure of the Mysterious Picture,” shot on-location in Van Cortlandt Manor! Tickets are $18, or $13 for Historic Hudson Valley members. Performances begin October 5. To go super-retro, drop by The Picture House in Pelham on Saturday, October 13 for a special screening of 1922 O.G. vampire flick Nosferatu, with a live score performed for the third year in a row by orchestral rockers The Invincible Czars. Tickets are available at the box office for only $15 for GA and $12 for students and seniors.


Visit an Actual Haunted House

Amityville ain’t got nothin’ on Westchester. Some of our towns predate the country so we’ve got quite a few old souls still mulling about our neck of the woods. If you don’t feel like breaking out the Ouija board and inviting them into your own house, why not meet them at theirs? We’ve got a number of supposedly haunted buildings and places throughout Westchester that should sufficiently spook. Heck, one of them is so popular, it even spawned its own movie! Yonkers alone has a few creepy sites, including Son of Sam’s alleged hangout, Untermyer Park!

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Related: You Can Finally See Buckout Road, the Horror Film Based on the Most Haunted Road in Westchester

Go Out of Your Gourd

Photo by Dave Zucker

The Great Jack O’Lantern Blaze in Croton-on-Hudson is a little touristy, yes, but when those tourists count Neil Patrick Harris and Laura Prepon amongst their ranks, do you really care? Huge installations of thousands of carved pumpkins light the night, and guests come from far and wide to gawk at cartoonish critters, life-sized dinos, the Statue of Liberty, and a working pumpkin carousel, and walk over the “Pumpkin Zee”—not “Cuomo”—Bridge. The Blaze has its opening weekend starting Friday, September 28, and is then open daily from October 4 through November 4 (and then sporadically through November 24). Tickets are $22 for adults and $16 for children 3 and older. (Historic Hudson Valley Members can attend any date and time for free.)

Related: Here’s a Peek at the Great Jack O’Lantern Blaze’s Newest Displays

Get Your Pants Scared Off

Kids love haunted houses and spooky hayrides, but sometimes adults like to be the ones at risk of peeing their pants. Open Fridays through Sundays in October, The Haunt at Rocky Ledge is a White Plains classic, taking you through spooky woods to haunted houses teaming with the dead and undead. Tickets are $25. Similarly, Horseman’s Hollow is another Historic Hudson Valley attraction at Philipsburg Manor, but one that is decidedly not family friendly. Take the haunted trail, stumble through a town of the insane, then try to make through the labyrinthine ruins of Ichabod’s Schoolhouse and the lair of the dreaded horseman himself…. Again, open extended weekends in October; Friday and Sunday tickets are $20 while Saturdays run $25. FastTrack tickets are $15, and HHV members save $5. Scared on the Sound at Rye Playland is a great option for older kids (generally 10+) and even adults who are ready for a little bit more fright than they neighborhood spook house. $20 per person.

When All Else Fails, Spit Out the Silver Bullets and Join the Pack

jefwod | Adobe Stock

Okay, fine, you can’t actually become a werewolf for Halloween. Sorry. But! You can do the next best thing, which is to go out and howl with real live wolves (and then go back to your nice warm house because you are still a soft, fur-less human and central heating is your friend). The Wolf Conservation Center in South Salem offers a pretty much year-round calendar of events and photo ops with their “ambassador” wolves, but none are more fun than an Evening Howl. Pair refreshments with some fascinating background on America’s native wolf populations and their conservation, then take a leisurely stroll through the night air to meet the wolves in person, howling—as you do—to announce your arrival to our canine masters. They’re beautiful, elegant, and highly carnivorous creatures, and you can attend Halloween Parties with them on the afternoons of October 27 and 28 for $14 ($11 for kids under 12), or take in a regular Howl on the 26th or 27th for $16/$13. (“Adults only” howls just mean there’s wine available, FYI. $20 for those.)

Our Westchester Home Design Awards event is June 26!

Our Wine & Food Festival returns June 4-9!

Our Wunderkinds event takes place on May 23!

Our Best of Business Ballot is open through May 15!

Our Healthcare Heroes Awards event takes place on May 9!

Our Westchester Home Builders Awards take place on April 4!

Our Diversity, Equity & Inclusion Forum is March 14!

Unveiled: A Boutique Bridal Brunch is February 25!

Our Best of Westchester Elimination Ballot is open through March 6!

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