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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. You can purchase tickets through the website.

Date: September 30, October 2, 7-9, 14-16
Where: 60 Continental St, Sleepy Hollow
Cost: $30 online, $40 at door

That’s (Not) All She Wrote 

This performance celebrates the work of local women playwrights. They will spotlight a selection of plays and monologues for a staged reading presented by the writers themselves. The actors will touch on a range of genres including sly comedies and compelling dramas. Each play was written by local playwrights and Westchester Collaborative Theatre members.

Date: October 1 & 2
Where: Westchester Collaborative Theatre, Ossining
Cost: $10

The Great Leap 

This performance tells the story of a young boy who plays basketball in Chinatown in San Francisco. Manford Lum eventually earns playing time on a college team in 1989 when the team travels to Beijing for a “friendship” game. At this point in time, China is in the midst of the post-Cultural Resolution era during which Manford must balance international politics and his personal history.

Date: October 1, 7, 8, 14, 15 & 16
Where: Arc Stages, Pleasantville
Cost: $28- $38


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The Prom

This Broadway and Netflix hit is taking the main stage at the White Plains Performing Arts Center. If you’re into comedies, “The Prom” is the musical for you. The performance follows big Broadway stars who are determined to change the world. They hear word that trouble is starting in a small-town because of its prom and immediately know this is something they can resolve. Although this is a musical comedy, the show touches on a universal message with which the audience can relate. If that doesn’t sell you, this play received seven Tony Award nominations and won the Drama Desk Award for Best Musical.

Date: October 7-23
Where: White Plains Performance Arts Center, White Plains
Cost: $45-$62


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Dracula & The Theatre of Doom

Sleepy Hollow’s own Peter Royston is keeping 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 audiences 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 7, 9, 16 & 31
Where: Tarrytown Music Hall, Tarrytown
Cost: $31

Related: Westchester’s Artistic Venues Are Hubs for Creativity and Culture


This show is presented by the Clocktower Players and features a star-studded cast of both Broadway and regional talent. The fall theater performance will start Clocktower Players’ 45th season off on the right foot. The group was selected as one of New York State’s “5 Best Community Theatre Companies” and one of Westchester’s best local theater groups. Clocktower Players is a charitable nonprofit organization that accepts donations to keep its artistic and educational programs on the rise.

Date: October 14
Where: Tarrytown Music Hall, Tarrytown
Cost: Starting at $75

Broadway Divafest

This performance will showcase the talents of five Broadway leading ladies who have performed in shows like “Wicked,” “Mamma Mia!,” “The Lion King,” and many more. It is produced and hosted by New York casting director Stephen DeAngelis and curated specially for the White Plains Performing Arts Center. The audience will get a highlight reel of the cast’s most memorable musical moments and career peaks. The cast will also share behind-the-scenes anecdotes and hold a Q&A for the audience.

Date: November 19
Where: White Plains Performance Arts Center, White Plains
Cost: $50-$66


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