13 Halloween Events in Westchester for All Ages

There’s no more appropriate place than Westchester County for the story of The Legend of Sleepy Hollow to be told. And no better time of year than right now. As “legend” says, it’s when Ichabod Crane and Brom Bones competed for the love of Katrina Van Tassel, all while the Headless Horseman looms in the distance. Arts groups throughout the County are putting their spin on the Legend tale, along with glowing jack o’lanterns, spooky storytimes, bone-chilling films and more. Read on for Halloween events in Westchester that will get people of all ages in the mood for a trick or treat of their own.

Through October 29

The Spirits of Sleepy Hollow Country

Presented by Historic Hudson Valley

Historic Hudson Valley presents a new event for this Halloween season, as illusionists Mark Clearview and Nick Wallace take their audience through the realm of the supernatural. Their tricks will have guests communicating with the long-departed spirits of Sleepy Hollow. At Philipsburg Manor. (381 N Broadway, Sleepy Hollow).

Photo by Liflander Photography

Through October 29

The Legend Cirque

Presented by Westchester Circus Arts and the Village of Sleepy Hollow

The Legend of Sleepy Hollow is reimagined in a cirque performance in Sleepy Hollow. Back for its second season, the show brings the Legend to life through acrobatic feats while telling the story of Ichabod Crane, Brom Bones, Katrina Van Tassel and the Headless Horseman.  (60 Continental Street, Sleepy Hollow)

Through October 31

Irving’s ‘Legend’

Jonathan Kruk performs Irving’s Legend at  Sunnyside.

Presented by Historic Hudson Valley

This year’s annual Irving’s ‘Legend’ event will be reimagined outdoors at the author’s former estate, Sunnyside. Master storyteller Jonathan Kruk will present dramatic performances of the classic Legend of Sleepy Hollow tale with live music accompaniment. The event may even include an appearance from the Headless Horseman. This experience is appropriate for all ages. At Washington Irving’s Sunnyside. (3 W Sunnyside Lane, Irvington)

Through November 12

Home of the ‘Legend’

Presented by Historic Hudson Valley

Washington Irving set the tone for the fall season when he wrote The Legend of Sleepy Hollow. Guests can tour his house, which will be seasonally decorated. The family-friendly visit includes an original shadow puppet short film and games on the lawn. (3 W Sunnyside Lane, Irvington)

Through November 19

The Great Jack O’Lantern Blaze

Presented by Historic Hudson Valley

The Great Jack O’Lantern Blaze is back in the Hudson Valley for its 18th annual showcase of carved pumpkins and jack o’lanterns. Guests can see over 7,000 jack o’lanterns, all designed and hand-carved by a team of artists and arranged into intricate sculptural displays, like a carousel, bridge and giant spider. At Van Cortlandt Manor. (525 S Riverside, Croton-on-Hudson)

October 14

Film Screening: Coraline

Presented by Jacob Burns Film Center

This film screening invites kids to watch the story of Coraline and the secret alternate reality she finds in her new home. Kids are encouraged to dress up in costume for the opportunity to take home prizes. After the Coraline screening, the Jacob Burns Film Center will also include a free clay sculpture activity, where kids will be able to make their own seeing stone. (364 Manville Road, Pleasantville)

October 16

Author Storytime: The Goblin Twins

Presented by Warner Library

Author Frances Cha will visit the Warner Library for a seasonal children’s storytime. The author will read her new book, The Goblin Twins, about two goblin tricksters who go on a Halloween adventure to New York, and present a related activity for them to partake in. At Warner Library (121 N Broadway, Tarrytown)

October 19-22, 26-29

Lyndhurst After Dark

Presented by Lyndhurst Mansion

This event takes guests through the historic Lyndhurst Mansion after dark. The estate will be decorated in the spirit of Halloween. Visitors can experience a darker side of the mansion through décor, architecture and collection items as performers regale them with tales of traditions and superstitions from the past. (635 S Broadway, Tarrytown)

October 27

Halloween Movie Marathon VII

Presented by Jacob Burns Film Center

Teens and adults will be taken through a classic Halloween movie marathon, featuring seven horror films, such as The Blair Witch Project and Halloween. The event will run all night, and will include a costume contest during a pre-marathon reception along with giveaways and other trick-or-treats to be announced. (364 Manville Road, Pleasantville)

October 28

A Twilight Zone Experience

Presented by Larchmont Library

The Larchmont Library presents a live “audio theater” performance and recreation of an episode of the classic 1959-1964 Twilight Zone television show. The episode “The Monsters Are Due on Maple Street” will be performed by the Sandbox Theatre. The event invites an audience of Twilight Zone fans and aficionados of all things eerie, including those who are visually impaired. (121 Larchmont Ave, Larchmont)

October 28-29

Halloween Weekend for the Kids

Presented by the Westchester Children’s Museum

The Westchester Children’s Museum is holding a Halloween Weekend event for kids aged 0-13. Some activities include Name ‘dem Bones, where kids will examine skeletons of various animals; Spider Web Engineering, where kids will make a web out of yarn and test its strength; and Ghost Pour Painting, where kids will get to create a spooky painting. (100 Playland Pkwy, Rye)

October 28-29

Concert: Halloween Classics by Candlelight

Presented by Fever

Fever presents the Highline String Quartet in a candlelight concert experience. This live music performance will be lit entirely by candles. This Halloween-themed concert will feature string quartet covers of various Halloween classics like Michael Jackson’s Thriller and Vic Mizzy’s The Addams Family theme song. At the Play Group Theatre. (1 N Broadway, White Plains)

October 29

Halloweekend Celebration

Presented by Hudson River Museum

Hudson River Museum welcomes guests to celebrate Halloween with a slew of Halloween-themed activities during its Halloweekend. Guests can visit the planetarium for a spooky star show, create origami jack-o’-lanterns and get their hands on lots of candy. Guests are encouraged to come in costume. (511 Warburton Ave, Yonkers)

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