Westchester’s Top August Events To Check Out

Articles Editor Marisa LaScala’s favorite reasons to get out of the house this month.


August 17

All-Around Classic

Montgomery Place—a historic Classical Revival mansion in Red Hook, New York—is always a fantastic spot for seeing historic architecture and formal gardens. But for one day in August, it’ll also be home to a different kind of classic, as its grounds play host to an antique car show. For more information, visit

August 2

Sonic Two-for-One

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Caramoor’s Summer Music Festival may be winding down, but  the music certainly isn’t. Evidence: The double bill of the Pat Metheny Unity Group and Bruce Hornsby, who will appear together on August 2. Between the two of them, you’re likely to hear eclectic combinations of jazz, rock, bluegrass, pop, and American roots music, all in Caramoor’s gorgeous Venetian Theater

August 3

Arts Outdoors

Last month, the Hudson River Museum in Yonkers debuted a new, outdoor, Hudson River-facing amphitheater, along with a lineup of alfresco entertainment. If you haven’t found an excuse to go with your family yet, take them to see the Catskill Puppet Theater’s production of Hiawatha, about the famous Native American hero. The show features exquisitely carved puppets along with live music, and it’s free with museum admission. And, when you don’t feel like bringing the kids along, keep an eye out for the amphitheater’s live music nights on Fridays, and movies or comedy shows on Saturdays.

August 6-7

Python Reunited

Nobody ever expects…Monty Python to do live shows together again. (Betcha thought we were going to say the Spanish Inquisition, eh?) Well, they are doing just that, and the Alamo Drafthouse Cinema in Yonkers will screen Monty Python Live (Mostly), broadcast from London’s O2 Arena. 

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August 13-14

He’s Alright

If the feeling strikes and you’ve got to cut loose, you’ll have two chances to get footloose with Kenny Loggins this month. He’ll perform on August 13 at the Ridgefield Playhouse in Ridgefield, Connecticut, and on August 14 at the Paramount Hudson Valley in Peekskill. No matter which performance you attend, you’re bound to hear some favorites from one or more of Loggins’ 12 platinum albums. 

August 2

Chalk It Up

If you thought your little artists were brilliant just because they could draw a hopscotch grid on the sidewalk, wait until you see what sidewalk chalk can really do. Head to the Cross County Shopping Center in Yonkers for the Sidewalk Chalk Art Festival, with a theme of “The 1950s,” as part of its 60th anniversary SummerFest. Prepare to be awed.

August 2

A Roll of the Dice

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Just when it seemed like comedian Andrew Dice Clay was fading into the background, he co-starred in, of all things, a Woody Allen move, Blue Jasmine. You know, it’s the one that got Cate Blanchett the Oscar. (Who would ever think you’d see the words “Andrew Dice Clay” and “Oscar” so close together?) But just because he’s branching out, it doesn’t mean he’s softened his act—as he’ll demonstrate when he performs at the Paramount Hudson Valley in Peekskill. 

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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