8 of the Coolest Things to Do in Westchester This October

Our favorite reasons to get out of the house this month.

Oct 2

King of the Capitol

Check out The Capitol Theatre in Port Chester to see Larry King & Everybody Who Was Anybody for the Past 50 Years, featuring media personality Larry King in a conversation about live music with The Capitol Theatre owner Peter Shapiro. Don’t miss the award-winning broadcaster and interviewer as he takes the stage in Westchester this month to discuss the history of Shapiro’s long-running Port Chester institution.

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Oct 3 – Nov 3

Stop and Shop

After mild-mannered Seymour Krelborn is thrust into the limelight upon discovering an extremely unique plant, a host of hilarious hijinks, celebrated songs, and unlikely dangers ensue. The Little Shop of Horrors, staged by Ridgefield’s ACT of Connecticut, blends comedy, rock, and horror to great effect and is known for catchy tunes like “Feed Me,” “Somewhere That’s Green,” and “Suddenly Seymour.”


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photo by Breeanne Clowdus

Oct 4 – Nov 3

Horseman of Horror

Embrace the Halloween spirit during The Sleepy Hollow Experience at Washington Irving’s Sunnyside, in Tarrytown, home of the iconic author who penned “The Legend of Sleepy Hollow.” Following numerous critically acclaimed performances around the country, this outdoor immersive theater event will finally make its way to the region. The interactive adventure features live singers, musicians, and storytellers who guide audience members around the estate to witness captivating performances and a thrilling encounter with the Headless Horseman himself.


Photo by harald krichel courtesy of wikimedia commons

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Oct 9

David the Goliath

Don’t miss out on the opportunity to hear humorist, author, and all-around-wit David Sedaris read from his New York Times bestselling collection of essays Calypso. Sedaris’ witty social critiques and satirical mastery has put him near the top of the cultural zeitgeist, and audiences will likely see why during this reading, which will be followed by audience questions. For those who want to meet the maestro in person, a book signing will be held both before and after the event.


Oct 11 – Oct 27


Stop by the White Plains Performing Arts Center and journey into a fantastic realm of music and adventure. Garnering both a Tony and Grammy Award for its renowned score, Tim Rice and Elton John’s AIDA tells the story of a Nubian princess, stolen from her land, who falls for an Egyptian commander. Featuring a host of beloved songs, as well as a pulse-pounding plot, this celebrated play is  worth a watch.


Oct 12

Let’s Glow

Experience the magic of Lightwire Theatre’s eye-popping illuminations this month during Moon Mouse at Mamaroneck’s Emelin Theatre. Aimed at family members of all ages, the show combines puppetry and technology to create a cutting-edge, luminescent spectacle in total darkness. The production follows Marvin the Mouse as he adventures into space and explores the surface of the moon. Witness the glow-in-the-dark theatrical artistry that was featured as a semifinalist on NBC’s Americas Got Talent, in Westchester.


Oct 24

Time Warp

Step back in time to the low-budget, cult classics of the 1970s with The Rocky Horror Picture Show, screening this month at Stamford’s Avon Theatre. Following an unwitting couple who find themselves in a freaky and fabulous mansion full of strange guests, the rare screening will also feature a costume contest along with prizes. Warp on over to this weird and whimsical musical for a late-night thrill.


Tunji Adeniyi-Jones, Blue Dancer (detail), 2017. © Tunji Adeniyi-Jones

Through December 7

Black Is Beautiful

Catch a deeply significant exhibition of African American art on show through December 7 at Concordia College’s OSilas Gallery. Free and open to the public, Young, Gifted and Black: The Lumpkin-Boccuzzi Family Collection of Contemporary Art features more than 40 important, early-career works by acclaimed artists of color, produced over the last 35 years. Don’t miss out on this beautiful dedication to generations of African American masters at this singular Bronxville show.

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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