7 of the Coolest Things to Do in Westchester This May

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

photo by JSquared photography

May 2

The Wolf of Tarrytown

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Few comedians have quite the cache of Michelle Wolf. The Emmy-nominated standup sensation famous for her no-holds-barred humor produced, wrote, and hosted her own Netflix show, The Break with Michelle Wolf, and was the subject of her own HBO standup special. Now, the comic is taking the stage at The Tarrytown Music Hall, where she will undoubtedly show just why she remains one of the boldest voices in comedy today.


photo by tim llewellyn

May 10

Cole Blooded

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Ever wonder what happened to the woman who sang “Where Have all The Cowboys Gone?” Well, she is stopping by Mamaroneck’s Emelin Theatre this month for a rare area performance. Paula Cole, who remains a respected jazz-and-folk singer, is touring on the release of her album, Ballads, which examines her varied musical influences, ranging from Billy Holiday to Bob Dylan.


May 11

Jazz Man

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The Caramoor Center for Music and the Arts remains one of Westchester’s most eye-catching musical venues, and what better way to soak in the scenery than with the dulcet sounds of the Edmar Castañeda Quartet? The Colombian-born eponym and harp virtuoso has penned symphonic works for the Orquestra Clássica de Espinho and the São Paulo Jazz Symphony Orchestra, as well as chamber pieces for the Orquestra Sinfónica Nacional de Colombia. Now, he and his quartet are stopping by Katonah for a single night of Columbian, Venezuelan, and Argentinian music.


photo by JSquared photography

May 15

King of Late-night

With 60 years on the small screen, interviewing pretty much everyone from Lady Gaga to the Dalai Lama, Larry King makes for some interesting talk. This month, the TV legend sits down with Peter Shapiro, owner of The Capitol Theatre, to discuss King’s life and work, as well as his perspective on live music and the Port Chester venue. Stop by The Cap for an evening of cutting-edge conversation.


Image courtesy of jacob burns film center

May 16

Highway to Hal

Time to open the pod doors and head to Pleasantville’s Jacob Burns Film Center for a rare “unrestored” screening of Stanley Kubrick’s seminal masterpiece 2001: A Space Odyssey. Supervised by acclaimed Dunkirk and Inception director Christopher Nolan, the new version was struck from the original camera negative of the film and is devoid of digital effects, edits, or remastering — making it about as close as one can get to the way it was first experienced in 1968.


May 29 – June 2

Lights, Camera, Advocacy

Each year, movie buffs from across the country gather in our region for a truly unique showcase of full-length features, short films, panels, and a wealth of other screenings and events. Celebrating its fifth anniversary, The Greenwich International Film Festival will overtake theaters and venues throughout Greenwich and the surrounding area, with dozens of advance screenings, film premiers, networking events, and, of course, star-studded parties.


Herb Snitzer (American, b. 1932). Nina Laughs, 1959. Gelatin silver print. Museum of Fine Arts, St. Petersburg.
Gift of the Artist in honor of the Museum’s 50th Anniversary and in memory of Nina Simone

May 30 – August 18


This lovingly curated exhibition on show from May 30 to Aug 18 at The Hudson River Museum in Yonkers shows off work by one of the most underappreciated modern American photographers alive. Can I Get a Witness: Photographs by Herb Snitzer features more than 45 images by the TIME-, LIFE-, and Fortune-published photographer, famous for his careful portraits of legendary jazz musicians and individuals hailing from virtually every walk of life.

Our Best of Westchester Party is July 24!

Our Westchester Home Design Awards event is June 26!

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!

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