October's Best Bets In Entertainment

All That Jazz – October 3

Even those who aren’t jazz fans can appreciate the style of Kellylee Evans, who’s bringing her smoldering sounds to the Emelin Theatre on October 3. This up-and-coming queen of the stage blends soul, hip-hop, pop, and jazz to create her own style and one unforgettable performance. Lest you think she’s not getting her dues, the Canadian singer has already racked up two Juno Award nominations for a pair of solo albums—not to mention she’s opened for such megastars as John Legend and Willy Nelson.

By the Book – October 3 

There is nothing better than curling up with a great book. Nothing, except maybe curling up with your child and watching their face light up as you read to them. Pick up some prime material at the Chappaqua Children’s Book Festival, one of the largest events of its kind in the metropolitan region. More than 85 renowned children’s book authors and illustrators will be on hand to sign books, read, and demonstrate their craft. Find books for sale, enter a raffle, and feed your family at the “Food for Thought” food truck court. Make sure you don’t leave without buying a treat for your kids (and yourself) at The Great Chappaqua Bake Sale, which benefits Share Our Strength’s mission to end childhood hunger.

Art History – October 4-March 13

When it comes to years that changed the landscape of America, it doesn’t get much bigger than 1965. The assassination of Malcolm X, the Watts Riots, the march from Selma, and the passage of the Voting Rights Act all took place during this watershed year. The Neuberger Museum of Art curates a selection of works from its permanent collection, as well as loans from private collectors, to tell the story of this turbulent period. The exhibit, After 1965, which opens this month, isn’t just about the past. The glimpse into our social history is meant as a commentary on the lingering impact of the ’60s on our lives today. 

Raise Your Glass – October 6-24

When discussing American playwrights, it is nearly impossible to avoid bringing up Arthur Miller and the monumental influence he’s had on modern theater. In honor of this tremendous talent’s 100th birthday (Miller was a longtime Connecticut resident), the Westport Country Playhouse is staging one of his most striking and powerful plays, Broken Glass. Set in New York City, the play details a married couple’s reaction to the sudden horrors of Nazi Germany. But do those reactions also mirror the couple’s own emotional issues? Broken Glass illuminates the struggles at the heart of both personal fear and romantic love, as well the remarkable horrors man is capable of. 

Seriously Funny – October 16

Rarely does the reigning king of wit descend to grace mere mortals with his presence. Well, get ready to bow before America’s leading humorist (and bestselling author) when David Sedaris hits the stage at the Tarrytown Music Hall on October 16. With 10 million copies of his books in print and his sardonic jokes translated into 25 languages, Sedaris definitely knows how to crack a few laughs. We know that smiles won’t be in short supply when he lets loose on stage, but beware: Expect nothing to be spared by Sedaris’ razor-sharp wit.

She’s Hip – October 24

Wish you were around when nightclubs were ruled by divas instead of DJs? Turns out those days aren’t gone for good; Ana Gasteyer takes the stage with a jazzy back-up band in her new performance I’m Hip! The comedic queen and Saturday Night Live vet transports the audience at Purchase’s Performing Arts Center back to the swingin’ splendor of days past. Gasteyer romps through risqué remembrances, belts out Broadway-style tunes, and shares a boatload of saucy stories. Don’t be surprised if you find some members of the Rat Pack drinking in the corner. 

Scare Tactics – October 30-31

How many film screenings involve costumed audience members toting rubber gloves, hot dogs, and rice? Only one—The Rocky Horror Picture Show. The ultimate cult classic comes to The Picture House in Pelham, where some of the area’s most eccentric film buffs will descend on what has become a Halloween tradition. First time? Don’t worry—no props are required at the showing of this sensationally weird testament to hokey musical numbers. Just watch as unsuspecting couple Brad and Janet find themselves in the clutches of Dr. Frank-n-Furter, a Transylvanian transvestite, and his cast of bizarre companions. Of course, for fans and first-timers, costumes are heartily encouraged.