The Hottest Westchester Happenings to Add to Your Calendar in May

Photo by Erin Baiano/ courtesy of the Emelin Theatre

A concert at Caramoor, a comedy night in Port Chester, and more are some of our favorite reasons to get out of the house this month.

Take a moment to unwind at the picturesque Caramoor Center for Music and the Arts on May 14, when talented singer-songwriter Eilen Jewell hits the stage for a night of her singular songs. With a style that blends early blues, surf noir, and classic country with folk and ’60s rock, Jewell has already released six celebrated albums and performed in venues from Australia to Spain.

Glittering Jewell

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May 6

Remembering an Icon

Selena was a skyrocketing star before her tragic murder in 1995, but this month, local audiences can celebrate her life when The Selena Experience overtakes Peekskill’s Paramount Hudson Valley Theater. Featuring acclaimed lead singer Genessa Escobar, backed by a group of talented musicians who originally joined forces on the 20th anniversary of Selena’s death, The Selena Experience provides a rare chance to remember an up-and-coming superstar.

May 10

One for Al

Through his sidesplitting song parodies, unique personal style, and sheer strangeness, “Weird Al” Yankovic has become an indispensable part of the American satirical musical landscape. With five Grammys and 14 studio albums — several of which have gone Platinum or Gold — as well as a slew of Billboard chart-topping hits, Yankovic will be making audiences smile this month at The Ridgefield Playhouse.

May 12

King George

Need a laugh? You’re not the only one. Luckily, comedy legend and former star of a hit eponymous sitcom, George Lopez is coming to the rescue, cracking wise this month at The Capitol Theatre in Port Chester. With his newest Netflix comedy special, We’ll Do It for Half, premiering over the summer, Lopez is also known for his four HBO comedy specials, TV Land show, Lopez, and years on the standup circuit.

The Capitol Theatre in Port Chester George Lopez
Photo Courtesy of The Capitol Theatre

May 22

Kid Stuff

Gather your children, even those with sensory sensitivities, and head to this fun family event in the open air. Dan and Claudia Zanes, Grammy-winning children’s performers known for crafting accessible songs for all ages, will be playing a sensory-friendly concert of loving folk music on the lawn of Katonah’s Caramoor Center for Music and the Arts for one super-fun evening this month.

May 13

Fancy Footwork

Get ready to experience the mesmerizing movement of The Mark Morris Dance Group. Called “the most successful and influential choreographer alive and indisputably the most musical” by The New York Times, Morris’ company of incredibly talented dancers have been drawing rave reviews since their 1980 founding and will be taking the stage at Mamaroneck’s Emelin Theatre for a night of daring dance.

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performance at Emelin Theatre
Photo by Erin Baiano/ courtesy of the Emelin Theatre

May 20

Free Williams

Hailing from Mount Kisco, Westchester’s own Dar Williams has been performing her signature brand of heartfelt folk for more than 25 years. This month, Williams will be taking the stage alongside noted singer-songwriter Sophie B. Hawkins for a soulful performance at Tarrytown Music Hall, where the two vocalists will demonstrate why they remain an enduring musical force.

May 20


It’s not every day that the prog-rock gods known as Primus take the stage in Westchester. Heading out on a tour celebrating the legendary late drummer of Rush, Neil Peart, these utterly unique musicians, led by cult-favorite singer and maestro bass player Les Claypool, will be taking the stage at Port Chester’s Capitol Theatre for rare evening performance.

performance at Port Chester’s Capitol Theatre
Photo Courtesy of The Capitol Theatre

Related: These Are the Best Things to Do in Westchester This Week

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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