The 8 Most Fun Things to Do in Westchester This June

Our favorite reasons to get out of the house this month


Photo by Adam Sommer

June 4-9

Dine Time

Food lovers unite! The county’s top celebration of everything edible comes to venues throughout the region with Westchester Magazine’s Wine & Food Festival. This seven-day blowout features seven mouth-watering events, ranging from a fun Food Truck Festival all the way to the mega-popular Burger & Beer Blast. Attendees can stop by swanky occasions like the June 8 Grand Tasting Village or even bring little ones to the lighthearted Jr. Chef Experience.

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Photo courtesy of NBC Universal Media

June 9

Funnyman Walking

Among SNL’s fleet of acclaimed alums, few score more popularity points than Seth Meyers. The host of NBC’s Late Night With Seth Meyers and former “Weekend Update” anchor, Meyers is known for his cutting satire and ultra-dry delivery. This month catch the celebrated comic in the flesh when he hits The Ridgefield Playhouse for a night of levity and laughter.


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Sara Cwynar, 72 Pictures of Modern Paintings, 2016, Digitally printed color wallpaper, Site specific, © Sara Cwynar, Courtesy of Cooper Cole, Toronto and Foxy Production, New York

June 9 – November 10

Art Darling

It’s difficult to describe the scope of boundary-pushing artist Sara Cwynar. The Canadian sensation runs the gamut from installations and photography to bookmaking and film. Now, Cwynar’s first solo exhibition on the East Coast comes to the Aldrich Museum of Art from June 9 to November 10. Visitors can spy a collection of the artist’s photographs, as well as her 16mm film, Cover Girl, a book, site-specific wallpaper, and other thought-provoking works.


Photo by Binkle_28, courtesy of Wikimedia Commons

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June 11-12

Dead Head

If seeing a member from one of the most acclaimed jam bands in history sounds like a good time, The Capitol Theatre has an event for you. This month, Phil Lesh & Friends will stop by the beloved Port Chester venue with famed guitarist Jorma Kaukonen for two nights of music harking back to the heyday of hippiedom.


Photo by Gabe Palacio

June 22

Find Your Roots

Katonah’s Caramoor Center for Music and the Arts is lovely almost any time of year, but it is truly something special in the summer. And there is no better way to ring in the season at this elegant venue than during its American Roots Festival. Featuring award-winning folk duo The Milk Carton Kids, the daylong fest includes a wealth of other acclaimed musicians, including Amythyst Kiah, Porch Stomp Review, and Deva Mahal.


Photo by Andy Scheller

June 27

All That Drag

June is Pride month, when everything LGBTQ+ is celebrated in cities across the globe. Get in on the festivities with this lighthearted event at The Bedford Playhouse, where the Patrick Swayze hit To Wong Foo, Thanks for Everything! Julie Newmar will be screened along with performances by two of the region’s most beloved drag queens, KiKi Lucia and Miss Frank.


June 27

Dude Tube

Is it possible for a film to grow in popularity, each year, forever? Probably not, but The Big Lebowski is certainly giving it a try. The cult obsession starring Jeff Bridges and John Goodman has spawned everything from movie marathons to its own real-life festival. Now, locals can check out The Dude in all his glory during this screening at The Avon in Stamford, which also includes a righteous costume contest.


Photo by Richard Termine

June 29

Puppet Master

This stage performance for both children and children-at-heart blends elements of Mister Rogers’ Neighborhood with Brooklyn-hipster style, along with a host of sidesplitting puppets.

The Joshua Show tells the story of a puppet named Mr. Nicholas, who is overcome by sadness and despair. It is up to Joshua and his band of merry friends to uplift Mr. Nicholas with songs, tap dancing, physical comedy, and several styles of eye-popping puppetry all onstage at the Tarrytown Music Hall.

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!

Our Best of Westchester Elimination Ballot is open through March 6!

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