The Hottest October Events Happening in Westchester County

Photo by Tom NYCZ For Historic Hudson Valley

The Great Jack O’Lantern Blaze, a spooky circus, a four-time Grammy Award-winning musical, and more make the month special.

By Katie Cristiano and Molly Reinmann

Ongoing through Nov 19

Pumpkin Paradise

Lovers of the spooky season can rejoice when The Great Jack O’Lantern Blaze overtakes Van Cortlandt Manor. Immerse yourself in a world of autumnal enchantment at this pumpkin extravaganza featuring more than 7,000 illuminated, hand-carved jack-o’-lanterns fashioned into a variety of interactive displays. Take a trek across the Pumpkin Zee Bridge, or see the stars only feet above your head in the glittering Pumpkin Planetarium.

Jack O'Lantern Blaze
Photo by Tom NYCZ For Historic Hudson Valley

Oct 18

The Horror!

Feel like you’ve stepped back in time when what many consider to be the world’s first horror movie receives a spooky soundtrack courtesy of live band, The Invincible Czars. The five-member ensemble adds a fun dimension and plenty of interesting sonic twists to the canonical German Expressionist film The Cabinet of Dr. Caligari, which tells the tale of a sleepwalker under the control of a nefarious figure, onscreen this month Yonkers’ Alamo Drafthouse Cinema.

Oct 22

Spooky Circus

Ever wondered if zombies can cartwheel? At The Vampire Circus a host of creepy characters engage in impressive gymnastics, and much more. The Tarrytown Music Hall is bringing back the spooky part-circus-part-theater production — replete with breathtaking acrobatics, funny quips, audience interaction, contortionists, jugglers, and comedians — which plays like an amusing cross between the work of Tim Burton and Cirque Du Soleil.

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The Vampire Circus
Photo courtesy of The Vampire Circus

Oct 6–22

New Heights

Hamilton creator Lin Manuel Miranda’s four-time Grammy Award Winning musical In The Heights is coming to Westchester. Catch this energetic production onstage at the White Plains Performing Arts Center, featuring a live orchestra backing up all the breathtaking costumes and sets. The musical tells the story of three generations living, learning, and falling in love in New York’s Washington Heights neighborhood.

In the Heights
Photo by Anna Louizos

Oct 13


Calling all fans of jazz and classical music! This fall, Grammy Award-winning jazz saxophonist Branford Marsalis is hitting the Performing Arts Center stage at Purchase College. Joined by the legendary music collective Orpheus Chamber Orchestra, Marsalis and company will perform a compelling program that blends jazz with classical music.

Oct 13 through Jan 14

Beast Mode

Come face-to-face with prowling panthers, magnificent horses, and dazzling peacocks in this animalistic exhibition on show at the Hudson River Museum from October 13 to January 14. A play on Charles Darwin’s scientific theory, Un/Natural Selections: Wildlife in Contemporary Art features multi-media works including animal imagery in contemporary settings, often with links to human civilization and our outsized impact on the natural world.

October events art
Peter Gerakaris (United States, B. 1981) Caravan (Owl), 2012. Oil on canvas. 84 x 84 inches. Purchased with funds generously donated by Adrienne and John Mars, National Museum of Wildlife Art. (c) Peter Gerakaris. M2016.042

Oct 19–22

Sustainable Scare

You’ve heard of a haunted house, but what about a haunted greenhouse? New Rochelle’s Wildcliff is combining spooky and sustainable this Halloween, with Dr. Wildcliff’s Haunted Greenhouse & Mansion. At Hudson Park, visitors can explore the creepy aftermath of Dr. Wildcliff’s vegetal catastrophe as they trek through an eerie corn maze and a supernatural greenhouse. The event is family-friendly and includes pumpkin doughnuts and hot chocolate for those who enjoy a sweet treat with the scares.

Oct 19–22, 26–29

Hair-Raising History

Experience Lyndhurst Mansion in all its ghostly glory this fall with Lyndhurst After Dark. Intrepid guests can tour the iconic Tarrytown manor while learning about Victorian mourning traditions through architecture and special collections pulled straight from the Gilded Age. After exploring winding stairwells and sneaking through creaky rooms, enjoy a delicious array of refreshments and snacks available for purchase to lift the spirits.

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Our Wine & Food Festival returns June 4-9!

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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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