5 Stellar May Events to Check out in Westchester County

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

The May events to check out in Westchester. © Photography by Robert Capa from the Robert Capa and Cornell Capa Archive at the International Center of Photography/ Magnum Photos.

A photojournalism exhibit in Yorktown, living art in Ossining, an author talk in Pleasantville, and more make the month unforgettable.

Photography May events
Sicilian Peasant Telling an American Officer Which Way the Germans Had Gone, near Troina, Sicily, August 4–5, 1943. © Photography by Robert Capa from the Robert Capa and Cornell Capa Archive at the International Center of Photography/ Magnum Photos.

Through October 8

Combat Photography

A picture is said to be worth a thousand words, but in the hands of Robert Capa, pictures are priceless. With his defiance of danger, Capa permanently broke the barriers of 20th-century war photojournalism and is today known as one of the greatest combat photographers of all time. Through October 8, Yorktown’s The Capa Space presents an engaging exhibition of more than 50 of his most iconic photographs. Take a step back in time and experience the triumphant and tragic stories of soldiers and civilians alike at This Is Robert Capa!

Art show May events
Elsa Rubenstein’s The Refuge of Sleep. Artwork By Elisa Rubenstein, Photo Courtesy of Ossining Arts Council.

May 12–21

Art in Action

This month, The Ossining Arts Council (OAC) and Westchester Collaborative Theater (WCT) join forces to present six original one-act plays accompanied by artwork from the OAC at the collaborative theater’s Black Box performance space in Ossining. The 2023 Living Art Event will take place on Fridays and Saturdays over its nine-day run and will include OAC member docents taking audiences through a gallery tour within the WCT’s performance space.

Jen Sincero Westchester May Events
Photo courtesy of the Jacob Burns Film Center.

May 4

Sincerly Sincero

A #1 New York Times Bestselling Author and motivational speaker who has sold more than five million copies of her funny, life-affirming books, Jen Sincero is heading to Pleasantville’s Jacob Burns Film Center for an inspirational talk as well as a book signing, meet-and-greet, and audience Q&A. Ticket purchases include a signed anniversary edition of Sincero’s newest book.

- Advertisement -

May 16

Red, White, and Blues

The creators of ’90s megahits like “Hook” and “Run-Around,” Blues Traveler have long been a household name, with 34 years of touring and 14 albums under their belts. The Grammy-winning, six-time Platinum rockers will be taking the Tarrytown Music Hall stage this month, along with special guest Vanessa Collier, for a night of jam-infused, harmonica-laden hits.

May 25

Laugh Masters

Anyone in need of a laugh may want to head to Bedford Playhouse this month, where a side-splitting force of comedic experts is assembling. Stars of Latenight Comedy features three entertainers from a host of well-known shows, including Cory Kahaney from America’s Got Talent and Last Comic Standing, Brian Scott McFadden of CBS’ The Late Show, and The Tonight Show’s Mike Vecchione.

Related: The Capa Space Debuts Westchester’s Newest Photography Gallery

Unveiled: A Boutique Bridal Brunch is February 25!

Holiday flash sale ... subscribe and save 50%

Limited time offer. New subscribers only.

Our Best of Westchester Readers' Ballot is open through January 10!