The Ultimate Westchester Halloween Bucket List

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

Jag_cz | Adobe Stock

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 through November 3. 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 17 through 31. New this year is the Sleepy Hollow Experience, interactive theater hosted right at Washington Irving's Sunnyside residence. Tickets for non-members are $45 for adults and $25 for kids 3 to 17.


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.

Starting September 28 this year, the Westchester County African American Advisory Board's Committee Commemorating African American History in Westchester is teaming up with the Jay Heritage Center and Friends of the African American Cemetery to host docent-led tours of Rye's iconic African American Cemetery.

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 sixth year, $60 (or $50 for students and JBFC members) will get you in for a preview screening of The Lodge, a MST3K-esque showing of Chopping Mall with live commentary by the cast of "We hate Movies," Astro-german Hagazussa, Indonesian-Korean production Satan's Slaves, Wes Craven's seminal A Nightmare on Elm Street, the not-even-remotely-final Friday the 13th: the Final Chapter, the Wind, Bliss, holiday classic Black Christmas, and recent Japanese sensation One Cut of the Dead. This year’s date is October 25. 

North-county film lovers can also hop the border into Carmel for the House of Horror Film Festival, featuring a selection of recent short (read: "30 minutes or less") horror films. This year the festival weekend is Saturday and Sunday October 12 and 20 and includes four screenings sessions for $8 each on Saturday, culminating with a feature presentation of the Lost Boys at 8 p.m. Sunday brings a costume party with snacks and a goody bag for kids starting at 3:30 p.m., heading into a showing of the far more age-appropriate The Nightmare Before Christmas.

To harken back to the golden age of Hollywood, also consider the following: One of the newest and most popular attractions 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 $15, or $10 for Historic Hudson Valley members.

Performances begin October 4. To go super-retro, drop by The Picture House in Pelham on Friday, October 11 for a special 7 p.m. 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!

Tarrytown Music Hall is even getting in on the action, giving guided ghost tours to all the weird and unexplained activity in the 130+ year old theater. Tours last about 45 minutes and cost $25.

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 is open weekends through September and is open daily from October 3 through November 3 (and then sporadically through the end of the month). Tickets are $23 for adults and $17 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 from October 4 through November 2, 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, but there is currently a buy one, get one free deal on The Haunt's website. 

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…. Open extended weekends from October 4 through November 3; Friday and Sunday tickets are $22 while Saturdays run $28. FastTrack passes are $15, and HHV members save $5. 

Hudson Horrors, a relative newcomer to the game, is setting up shop at Rye Playland with three haunted attractions — hospital, mansion, and creepy toy factory — and over 60 characters to scare you stupid. Tickets start at $39.99.

Scared by the Sound, also 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.


Be a Kid Again

No, we don't mean "T.P. your rude neighbor's house." (Sorry about that, Steve.) Halloween in Westchester is, fundamentally, for the children to go out, put on some fun costumes, and get some delicious, high sugar content treats. For some added fun, the nearby Greenwich Botanical Center is hosting Ghouls in the Garden on October 19, an afternoon of family activities, a costume parade, pumpkin decorating, a "spook walk" through the greenery, and of course some choice refreshments and prizes! Tickets start at $25 for adults and $15 for kids as part of early-bird pricing, and go up on October 6. (Members however can save an extra $5.)

LEGOLAND Discover Center in Yonkers is also getting in on the action this Samhain, with Brick-or-Treat running September 28 through October 27. Giveaways, "scare-venger hunts," themed builds, and plenty of brick-y ghouls hanging around. A new addition this year is the "Hidden Side" event that combines your trip to the LDC with the mystery of an AR ghost-hunting app!

The Caramoor Center for Music and Arts is also holding Spooky Tales on October 30 for kids aged 3 to 8. Dress up and come down for some cute and spooky stories and prizes, plus hot cider and cookies!


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 a Halloween Howl with them on October 25. This howl is "adults only," which means there's wine. Kids can attended Halloween Parties with the wolves, where holiday-themed goodies will be handed out to those with and without fur, on the mornings and afternoons of October 26 and 27. Tickets are $20 for the "adults only" howl and $14 for adults/$11 for kids under 12 for the parties. 



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