Your Fall Theater Guide for Westchester County

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Westchester County has an array of live theater performances for locals and visitors alike to enjoy all throughout fall.

Dive into the world of Westchester theater this fall! There’s no need to travel to New York City to enjoy a quality theater performance. Westchester has an impressive lineup of plays and spooky immersive experiences for you to attend in the upcoming months.

The Legend – Cirque Theatre Performance 

The Legend theater performance is here to get you into the Halloween spirit. Go back in time to the early 1800s to see a fresh rendition of “The Legend of Sleepy Hollow.” This is an immersive experience during which you will hear the clacking of metal horseshoes along cobblestone roads and witness the groundbreaking use of holograms. The performance is set in Sleepy Hollow and follows the tale of modern-day Irving telling us what he really meant by “the legend.” This is performed by Westchester Circus Arts and brought to you by The Village of Sleepy Hollow.

Date: October 7-9, 14-16
Where: 60 Continental St, Sleepy Hollow
Cost: $30 online, $40 at door

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Harold Pinter Play Festival

The Katonah Classic hosts its Harold Pinter Play Festival, which features three plays by Nobel Prize winner Harold Pinter. This weekend, attendees can catch a showing of Betrayal, a show that has won numerous awards. Betrayal dissects love and marriage with a sprinkle of humor, desire, and honesty. Tickets for this show cost $39 for adults and $29 for seniors, students, and veterans. Additional shows include Applicant/Dumbwaiter directed by Marilyn Fox.

Date: October 5-29
The Whippoorwill Theatre, Armonk
$39 for adults or $29 for seniors, students, and veterans

Marry Me a Little

This performance tells the story of two single New Yorkers who decide to spend their Saturday night alone in their apartments. All night they dream about finding the love they’ve been longing for. Then the question arises: could they be what the other was looking for all along?  The show is directed by Ann-Ngaire Martin with musical direction by Marcus Baker.

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Date:  October 6-7,13-15
Where: Arc Stages, Pleasantville
Cost: $10


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In the Heights 

In the Heights was created by Lin-Manuel Miranda, the creator of Hamilton. This four-time Tony Award-winning Best Musical comes to Westchester this autumn. The musical tells the story of a lively community in Washington Heights where the windows are always open, coffee is pouring, and hopes are high. Three generations of dreamers are in the midst of change, and their biggest struggle is figuring out which traditions to take with them and which to leave behind.

Date: October 6-29
Where: White Plains Performance Arts Center, White Plains
Cost: $47-$65


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Dracula & The Theatre of Doom

Sleepy Hollow’s own Peter Royston keeps the audience on its feet with his play, “Dracula.” This is another interactive play as Dracula, the king of vampires, runs around the Music Hall using it as his backdrop. The actors will take the audience under the stage, then back up to the towering balcony for their dramatic reveal. You won’t want to miss out on this spooky tale.

Date: October 15, 29, 31
Where: Tarrytown Music Hall, Tarrytown
Cost: $36

Bat Boy: The Musical

This horror comedy tale is based on a story on The Weekly World News about Bat Boy. When a half-boy, half-bat creature is found lurking in a cave near Hope Falls, West Virginia, the local sheriff brings him to the home of the town veterinarian. His wife and daughter eventually accept the bat boy as their own and teach him how to act like a “normal” boy.

Date: November 10-19
Where: Arc Stages, Pleasantville
Cost: $22- $28


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Broadway Family Favorites

The White Plains Performing Arts Center hosts a Broadway show for the whole family. Explore everything musical theater has to offer through songs, lovable characters, and cheerful dancing this fall. This event was created and hosted by Producing Artistic Director Stephen DeAngelis. Plus, four well-known, versatile Broadway performers including Major Attaway, Todd Buonopane, Jessie Hooker-Bailey, and Teal Wicks will take the stage.

Date: November 25
White Plains Performing Arts Center

Related: The Hottest October Events Happening in Westchester County

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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