Halloween Events in Westchester to Shock, Scare, and Startle

Scary stories, historic haunts, and spooky movie nights will keep you entertained all month with the best Halloween events in Westchester.

As October rolls around each year, it’s time to embrace the chills brought on by the weather and all the spooky activities. There are a variety of Halloween events for every member of the family to enjoy. Whether you love scary movies and ghost tales from the past or you’re not a fan of all the scares, there’s an option for everyone on this list.

LEGOLAND’s Brick-or-Treat

LEGOLAND Discovery Center Westchester at Ridge Hill Mall, Yonkers
Through October 31

For the kids, there’s nothing like a day full of spooktacular activities at Legoland. They can choose from a scavenger hunt, the chance to create their own magical potion, meet-and-greets with characters, and more. The Brick-or-Treat activity allows kids to team up with Master Model Builder for a special Halloween build. Entry comes with general admission of $29.99.

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The Great Jack O’Lantern Blaze

Van Cortlandt Manor, Croton-on-Hudson
Through November

Prepare to be amazed during this annual celebration of all things pumpkin. Ringing in 20 years of fun, this popular Halloween extravaganza takes over the grounds of Croton-on-Hudson’s Van Cortlandt Manor each year with roughly 7,000 hand-carved, illuminated jack-o’-lanterns in a dizzying array of forms — from a pumpkin carousel and bridge to an immersive river display — all enlivened by synchronized lighting and a ghostly original soundtrack.

blaze - halloween events
Courtesy Historic Hudson Valley

Related: Everything You Need to Know About Croton’s Great Jack O’Lantern Blaze

Irving’s Legend

Philipsburg Manor, Sleepy Hollow
Through November 3

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There are few better ways to kick off the spooky season than with a time-tested retelling of Washington Irving’s tale, “The Legend of Sleepy Hollow.” Master storyteller Jonathan Kruk will bring this seasonal story to life with an under-the-stars performance of the iconic tale at Washington Irving’s Sunnyside in Tarrytown. Entertained by live music and an appearance from the headless horseman himself, Halloween hounds will likely find a lot to love at this literary occasion.

halloween events westchester irving's legenf
Courtesy of Historic Hudson Valley

The Spirits of Sleepy Hollow Country

Philipsburg Manor, Sleepy Hollow
Select dates through November 3

For a touch of magic in Sleepy Hollow, this Historic Hudson Valley event filled with brow-raising feats and more than a little mystery leans into the folklore that surrounds Westchester County. Master illusionists Mark Clearview and Nick Wallace lead visitors on a journey through the history of famed figures like Washington Irving, Hulda the witch, and the headless horseman, all while enchanting the audience with acts that boggle the mind.

Twilight Village at Sleepy Hollow

Philipsburg Manor, Sleepy Hollow
Through November 3

Come one, come all to this chilling village populated by mysterious creatures willing to tell guests’ fortunes, croon creepy tunes, and recite hair-raising tales replete with local lore. Halloween lovers can shop for Sleepy Hollow swag during the event’s Halloween night market or tuck into a coven of cocktails, mocktails, and snacks. But be warned, the headless horseman himself may be afoot at this family-friendly affair.

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Twilight Village at Sleepy Hollow
Twilight Village at Sleepy Hollow. Photo by Tom NYCZ.

Ghost Tour of Tarrytown Music Hall

Tarrytown Music Hall, Tarrytown
October 2, 8-9, 15-16, 31; November 5-6, 10

Walk through the doors of the 139-year-old historic theater and uncover the unexplained happenings and paranormal activity, from mysterious lights to the sound of vocal scales after hours. This ghost tour will take you from “balcony to backstage” as you discover the theater’s past, secrets, and lingering guests. Tickets are $29.

The Octagon House, Myths & Mysteries Tour

The Armour-Stiner Octagon House, Irvington
Select dates from October 3 – November 3

Discover the magic and architecture of this 1860 historic home, known as the pride of the Village of Irvington. Gather around to hear stories of the house’s history and otherworldly experiences of the previous tenants. The tours last about an hour, and tickets are $29.

Read More: Where to Go Pumpkin Picking in Westchester County

Stew Leonard’s Halloween Happenings

Stew Leonard’s, Yonkers
October 4-31

Stew Leonard’s offers fun family Halloween events through October. From October 4 through the 31, the shop will have a family-friendly hay maze decorated with pumpkins, scarecrows, and festive inflatables. If you purchase a pumpkin between October 12-14, you are invited to a complimentary pumpkin-painting event under the Garden Shop’s tent. On Saturday, October 26 and Sunday, October 27, there will be a Halloween brunch with Wow the Cow and Friends for $19.99 per person. Head to Stew Leonard’s website for more information on the events. 

 

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HallowGlow Nights

Boundless Adventures, Purchase
October 4, 12, 19, 26

Put on your best costume and get ready to face the fall weather and enjoy the beautiful views. Get spooky at Boundless Adventures as you climb, swing, and zip through the forest with scary themed music playing. There will also be candy available for trick-or-treaters. Advance tickets are $57, and same-day tickets are $63 for two-hour climbs.

The Haunt at Wildcliff Mansion

Wildcliff Mansion, New Rochelle
October 11 – November 2

This immersive Halloween experience returns to New Rochelle, bringing with it a host of spooky fun. Guests can explore Dr. Wildcliff’s forgotten laboratory on select nights this month, where they’ll pass by frightening features, including a graveyard and cathedral, before attempting to escape the event’s haunted corn maze and the mansion’s twisting halls populated by ghostly figures and surprising horrors. Each night, the mansion brings in local food trucks (because, hey, getting scared can make you hungry).

25th Anniversary of Tim Burton’s Sleepy Hollow

Tarrytown Music Hall, Tarrytown
October 12, 4 p.m.

Drop by Tarrytown Music Hall for a screening of Tim Burton’s 1999 film Sleepy Hollow. There’s no better way to celebrate the film’s anniversary than by watching it in the historic music hall so close to where the tale takes place. Tickets are $18, and the movie is rated R. The music hall will also be screening the cult classic The Rocky Horror Picture Show on October 26 at 9:30 p.m. Tickets cost $28.

Lyndhurst After Dark

Lyndhurst Mansion, Tarrytown
October 17-20, 24-27

Experience the height of Gilded Age grandeur while delving into dark Victorian lore at this annual Halloween event on the grounds of Tarrytown’s Lyndhurst Mansion. Timed entry into the mansion allows visitors to brave a semi-guided tour exploring the darker side of history through the words and tales of those who lived there. Intrepid guests can experience the eerie architecture, decor, and displays of unlikely items relating to superstitions of the age as talented performers regale them with tales of the past.

Spooktoberfest 

Hart’s Brook Park & Reserve, Hartsdale
October 19, 12-4:30 p.m.

Ghostly greetings! Join the Town of Greenburgh Department of Parks and Recreation for the annual Spooktoberfest. Families will get to go on a Halloween hayride, enjoy the petting zoo, and make Halloween crafts. There will also be various food vendors for a bootiful day. Admission is $7, or free for children under the age of two.

Goosefeather Halloween Party

Goosefeather at the Tarrytown House, Tarrytown
October 26, 12-3 p.m.

Bring the family along for a day of fall festivities. Enjoy the costume contest, the candy hunt (at 12 p.m.), a bouncy house, and lawn games. Choose from a variety of plates and drinks, including popcorn, cotton candy, and apple cider. Tickets are $15, and admission is free for children ages nine and under.

Downtown Yonkers Pet Parade & Fashion Show 

Yonkers Waterfront Amphitheatre, Yonkers
October 26, 12-2 p.m.

Celebrate the Halloween season with the sixth annual pet parade and fashion show. Bring your pet in costume for a chance to win the scariest, cutest, or most creative costume. In addition, there will be a free video booth and gift bags for you and your pet.

Tarrytown Halloween Parade

Patriots Park, Sleepy Hollow
October 26, 5:30 p.m.

Off we go a-haunting for the 22nd annual Village of Tarrytown Halloween Parade march down Tarrytown’s Main Street. After that, head to the block party that follows with a DJ, outdoor dining, performers, and a chance to win prizes if you march with a theme as a group or float. Registration is required to be eligible for prizes.

Halloweekend

Hudson River Museum, Yonkers
October 26-27, 11 a.m. – 5 p.m.

Head down to the Hudson River Museum for multiple Halloween events that offer fun for the whole family. Choose from various activities, such as decorating your own finger monsters, enjoying a live animal show, or taking a tour of the Glenview home. There will also be the opportunity to learn about the stars in the museum’s spooky planetarium show at 2 p.m. Come in costume!

The Vampire Circus

Tarrytown Music Hall, Tarrytown
October 30, 8 p.m.

Tim Burton meets Cirque du Soliel in this macabre mashup of cabaret and theater on stage for one night only at the Tarrytown Music Hall. At once dark, mysterious, and full of cutting-edge tech, this singular production brings the spooky in spades with the multidisciplinary skills of its band of international performers adept in dance, theater, and gymnastics. Replete with terrifying clowns and macabre sets, this unique show is worth a watch for anyone with a soft spot for Halloween events.


Read More: 12 Westchester County Horror Films to Watch This October

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