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Your Fall Arts & Events Guide for Westchester County

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Photo  by Eduardo Pavez Goye / Courtesy of Caramoor Center for Music and the Arts

Whether you want a quick list of must-see acts or spots to create a little art of your own, look no further than this love letter to local culture.

Come one, come all to Westchester’s fleet of fantastic fall events. With venues across the county once again welcoming culture-hungry visitors, now’s the time to get in line for any one of the superior musical acts, art exhibitions, kids’ events, funky festivals, and much more in this rollicking roundup of local goings-on.

Hot List

Looking for the cream of the fall arts crop? No worries. Try this list of the county’s top events.

David Sedaris

Oct 8; The Performing Arts Center at Purchase College

Bask in the awe-inspiring wit of this famed humorist boasting a raft of best-selling books, including Me Talk Pretty One Day and Naked.

Dionne Warwick

Sept 11; Tarrytown Music Hall

Welcome this Grammy Hall of Fame inductee and iconic pop diva when she drops by Tarrytown Music Hall for a toe-tapping area performance.

Phil Lesh & Friends

Oct 14–16, 21–23, 28–29, 31; The Capitol Theatre

Former Grateful Dead bassist Phil Lesh is practically a Westchester local at this point, playing several shows each year at Port Chester’s Capitol Theatre. That means fans have plenty of time to catch the jam-band legend known for his psychedelic sound and energetic backing band during the nine nights he’ll be performing.

Phil Lesh art

Phil Lesh & Friends, Oct 14–16, 21–23, 28–29, 31; The Capitol Theatre. You’ll have plenty of time to catch former Grateful Dead bassist Phil Lesh when he performs nine separate shows of mind-bending psychedelic rock in Port Chester. Photo by Dino Perrucci / Courtesy of The Capital Theatre.

The Social Fabric: Common Threads and Uncommon Vision

Oct 12–Jan 23; ArtsWestchester

Textiles, fabrics, and garments are used as a launchpad to investigate issues of climate change, identity, consumerism, history, and language in this inventive exhibit.

Tracy Morgan

Oct 27; Paramount Hudson Valley Theater

Need a laugh? Inject a bit of levity into your life with the sidesplitting standup of this celebrated SNL and 30 Rock star.

Pilobolus

Oct 29; Emelin Theatre

This acclaimed dance company is celebrating its 50th anniversary during its Big Five-Oh! Tour, with a stirring program that pays homage to the company’s laudable career.

The Prom

Oct 7–23; White Plains Performing Arts Center

Take a trip back to the halcyon days of high school with this Broadway and Netflix hit musical nominated for seven Tonys and winner of a Drama Desk Award.

Violent Femmes

Oct 8; Tarrytown Musical Hall

The iconic rockers known for memorable hits like “Blister in the Sun,” “Add It Up,” and “Gone Daddy Gone” are bringing their signature brand of acoustic punk to Westchester.

Garrison Keillor

Oct 9; Paramount Hudson Valley Theater

The grass-roots entertainer of NPR fame will take the stage in Peekskill for an evening of storytelling, standup, song, and poetry.

Funky Fests

Those looking to let loose with a rollicking festival can take their pick from this lineup of exceptional area events.

The Great Jack O’Lantern Blaze

Sept-Nov; Van Cortlandt Manor

Ring in the spooky season with style during this celebration of all things pumpkin. Fall in Westchester wouldn’t be complete without a visit to this Halloween extravaganza that overtakes the grounds of Croton-on-Hudson’s Van Cortlandt Manor, with roughly 7,000 hand-carved, illuminated jack-o’-lanterns in a dizzying array of forms — from a pumpkin carousel to an immersive river display — all enlivened by synchronized lighting and a ghostly original soundtrack.

pumpkin blaze

The Great Jack O’Lantern Blaze, Sept–Nov; Van Cortlandt Manor. Photo by Tom NYCZ/ Courtesy of Historic Hudson Valley.

JazzFest White Plains

Sept 14–18; Various Locations

It’s high time for all that jazz. This annual fest presented by White Plains’ ArtsWestchester is back for the 2022 season with an in-person lineup comprising both nationally and regionally recognized jazz greats, as well as some of the genre’s hottest rising stars. Taking place in various locations throughout the county seat, JazzFest features performances by the François Moutin & Kevita Shah Duo, Bronx’s Albert Rivera Quintet, and the three-time Grammy-nominated Joey Alexander Trio, among several others.

Armonk Outdoor Art Show

Oct 1 & 2; 205 Business Park Dr, Armonk

Ranked among the best arts-and-crafts shows in America, this family-friendly outdoor event, now in its 60th year, once again descends on our region with a veritable tsunami of paintings, prints, sculptures, drawings, pastels, photography, fine art, and much more. With everything for sale in an open-air environment, visitors will also find food vendors, drinks, and a tent providing free activities for kids, including art lessons and fun projects.

Serious Fun Arts Fest

Oct 12–16; Various Locations

White Plains transforms into a wonderland of creativity during this five-day public festival featuring acclaimed performances in addition to the work of several renowned artists. This year, NYC-based band Sammy Rae & The Friends will headline the fest with an outdoor concert on October 16. New, monumental works of public art — including a two-story stainless-steel teardrop sculpture by Bulgarian artist Georgi Minchev and a nine-story fabric installation by Amanda Browder — will also be featured during this multi-venue event.

ArtsFest 2022

Oct 20–23; Various Locations

Featuring a host of exhibitions, activities, and programs held at dozens of venues throughout New Rochelle and Pelham, ArtsFest returns in top form. Organized by New Rochelle’s Council on the Arts, the expansive event includes music, artist workshops, dance performances, and an artisan market. On the first night, Copland House will help kick off the fest with the world premiere of a new work by composer Steven Snowden. Attendees can also enjoy a free guided trolley tour of New Rochelle’s 20 #NRNY Murals and a Friday-evening performance of works by George Walker, the first African American to win the Pulitzer Prize in music.

Fall Crafts at Lyndhurst

Sept 16–18; Tarrytown

Outfit your entire home with unique works of art during this autumn extravaganza at Tarrytown’s Lyndhurst mansion. This year’s event features 200 craftspeople filling the mansion’s expansive grounds with functional and sculptural works in wood, glass, metal, and ceramics, as well as paintings, prints, drawings, fashion, jewelry, photography, and more. Plus, there are plenty of additional reasons to haul the family over to Tarrytown, such as gourmet food trucks and tastings from local distilleries, wineries, and cider houses; children’s activities on Saturday and Sunday; and a silk-scarf hand-painting class.

Yellow Brick Road Fest

Oct 8; Bedford

Channel your inner Tin Man while supporting a good cause during this lighthearted family festival. Benefiting the 501(c)(3) Bedford Playhouse, this event celebrating The Wizard of Oz features kids’ activities, a Kansas-style picnic barbecue buffet provided by Pound Ridge Market, face painting, a costume prize contest, and of course the Judy Garland classic playing on the Playhouse’s state-of-the-art, open-air, 40-foot screen.

Music

From rock and pop to classical and jazz, here are our top picks of acts you should lend your ears to.

Rock, Pop, Hip-Hop & Fusion

Rufus Wainwright

Oct 2; Tarrytown Music Hall

The indie figurehead known for his expansive voice is making his way to the county during a solo tour supporting his first studio album in nearly seven years, Unfollow the Rules. Once named Best New Artist by Rolling Stone, Wainwright has remained in the spotlight, with 10 studio albums and contributions to numerous soundtracks and plays.

Phil Lesh & Friends

Oct 14–16, 21–23, 28–29, 31; The Capitol Theatre

Former Grateful Dead bassist Phil Lesh is practically a Westchester local at this point, playing several shows each year at Port Chester’s Capitol Theatre. That means fans have plenty of time to catch the jam-band legend known for his psychedelic sound and energetic backing band during the nine nights he’ll be performing.

Dionne Warwick

Sept 11; Tarrytown Music Hall

The word “legend” is too often thrown around, but in the case of Dionne Warwick, it fits. The six-time Grammy-winning icon has more than 75 hit songs to her name and was ranked one of Billboard Top 100’s “Greatest Artists of All Time,” not to mention 100 million records sold and 18 consecutive Top 100 singles. Now, locals can see this treasured chart-topper in the flesh when she lights up the stage in Tarrytown.

Violent Femmes

Oct 8; Tarrytown Music Hall

This cultish folk-punk band from Milwaukee set out to revolutionize acoustic rock, and it’s safe to say they were successful, having produced 10 studio albums, including their Platinum self-titled record, memorable hits like “Blister in the Sun” and “Add it Up,” and a rabid worldwide fan base.

Gangstagrass

Sep 24; Emelin Theatre

Brooklyn-based powerhouse group Gangstagrass blend bluegrass with hip-hop and other genres to create a truly unique and infectious sound. After performing at such events as SXSW, Americana Festival, and the Grey Fox Bluegrass Festival, Gangstagrass are bringing their singular vibe to Mamaroneck.

Gangstagrass

Gangstagrass blend elements of bluegrass and hip-hop. Photo by Melodie Yvonne/ Courtesy of the Emelin Theatre.

Colbie Caillat

Oct 23; The Ridgefield Playhouse

Colbie Caillat returns to The Ridgefield Playhouse this fall to celebrate the 15th anniversary of her breakout hit, “Bubbly,” which is still among the best-selling digital tracks in history. Today, Caillat remains a musical mainstay, having sold nearly six million albums, with two Grammy Awards, and performing alongside the likes of Sheryl Crow and John Mayer.

Steve Vai

Oct 27; The Capitol Theatre

With three Grammys, 15 million albums sold, and a career performing alongside music legend Frank Zappa, Steve Vai is one respected rocker. Named the 10th-greatest guitarist by Guitar World Magazine, Vai will be dropping by The Cap this season to show off some serious string theory.

Steve Vai music art

Steve Vai Oct 27; The Capitol Theatre. Photo by Larr Dimarzio/ Courtesy of The Capital Theatre.

Accept

Oct 22; Paramount Hudson Valley Theatre

These heavy-metal mainstays from Germany are prepared to rock. Taking the stage this fall in Peekskill, Accept first began their reign during the 1970s and have since grown to become an internationally respected band that helped originate the genre of thrash metal and inspired greats like Metallica in the process.

Joan Osborne

Nov 18; Tarrytown Music Hall

Joan Osborne found nearly instant fame a quarter-century ago with her megahit “One of Us,” which led to a multi-Platinum record and seven Grammy nominations. Touring upon the release of her 10th studio album, Trouble and Strife, Osborne is set to bring her music blending soul, roots-rock, blues, country, and pop to the county.

Classical, Jazz & World Music

Delfeayo Marsalis Quintet

Oct 1; Emelin Theatre

This Grammy-winning trombonist, producer, and composer took home the nation’s highest jazz honor, a National Endowment for the Arts Jazz Masters Award, alongside famous brother Wynton and the rest of the ultra-talented Marsalis family, in 2011. He has since been featured in Ken Burns’ documentary Jazz and remains an outsize figure in the genre today.

Glenn Miller Orchestra

Oct 22; Emelin Theatre

A star of 1930s and ’40s radio, Glenn Miller’s big band lives on to this day, with roughly 300 performances a year. They still dutifully crank out nostalgic retro gems, like “Chattanooga Choo Choo,” “Tuxedo Junction,” “Moonlight Serenade,” and “A String of Pearls.”

Jeremy Denk

Nov 6; Caramoor Center for Music and the Arts

The winner of an Avery Fisher Prize, as well as a MacArthur “Genius” Fellowship, Jeremy Denk was called “a pianist you want to hear no matter what he performs” by The New York Times. Luckily, local audiences can do just that when the multitalented memoirist and musician performs Bach’s celebrated Well-Tempered Clavier, Book I.

Melissa Aldana Quartet

Sept 30; Caramoor Center for Music and the Arts

With the recent release of her well-received album 12 Stars, Grammy-nominated saxophonist and composer Melissa Aldana has stepped into the spotlight. Come see why the Brooklyn-based tenor from Chile has been setting the world ablaze with her stirring music when she drops by Katonah this fall.

Melissa Aldana musical art

Melissa Aldana Quartet Sept 30; Caramoor Center for Music and the Arts. Photo Eduardo Pavez Goye/ Courtesy of Caramoor Center for Music and the Arts.

Kids’ Corner

Take the little ones out to these fun events tailored to tikes.

Wakanda Celebration

Sept 3; Luangisa African Gallery

Celebrate the culture and community of Africa during this annual Mount Vernon event ideal for the family. Inspired by the hit MCU film Black Panther and dedicated to illuminating the music, arts, and heritage of African Americans, this event stretching from 11 a.m. to 8 p.m. includes a wearable African-art fashion show, live band, dancing, drumming, African cuisine, kids’ activities, and a host of home goods and crafts for sale, handmade by African artisans.

Click Clack Moo

Dec 10; Emelin Theatre

Kids can learn the ins and outs of negotiation and compromise during this smart-yet-lighthearted family musical onstage at the Emelin. Click Clack Moo tells the story of Farmer Brown, who has to contend with some demanding livestock when the hens go on strike and the cows begin typing. Based on Doreen Cronin and Betsy Lewin’s Caldecott Honor-winning book, this TheatreworksUSA presentation offers kids and adults alike a surprisingly touching example of cooperation, concession, and negotiation.

MasterChef Junior Live!

Oct 11; The Palace Theatre

Ever wanted to experience the fast-paced magic of a cooking show in person? Foodies of all ages are invited to attend this interactive production bringing hit TV program MasterChef Junior to life onstage. Audiences can watch Season Eight winners, finalists, and fan-favorites going head-to-head in cooking demonstrations and partaking in amusing challenges that will likely make audiences feel as if they’ve entered their favorite TV show.

Dance

Experience a daring demonstration of dance this fall.

Paul Taylor Dance Company

Sept 7; The Pocantico Center

As part of the Rockefeller Brothers Fund’s Culpeper Performance Series, the internationally renowned Paul Taylor Dance Company will be bringing their fancy footwork to The Pocantico Center. Led by artistic director Michael Novak, the company will present a selection of their acclaimed repertory work with 1981’s Arden Court, which examines varying types of relationships through movement, and 1987’s Syzygy, in which dancers bound across the stage like unruly meteors, nearly crashing into one another.

Pilobolus

Oct 29; Emelin Theatre

With more than five decades of respected work, Pilobolus is taking the Mamaroneck stage to celebrate its 50th anniversary with a program of dance paying homage to its sweeping career. Keeping with its propensity to break with tradition and forge new paths, the company will present prior works radically reimagined for a never-before-seen night of audacious dance.

Nutcracker! Magic of Christmas Ballet

Nov 16; The Capitol Theatre

Producer Akiva Talmi presents the 30th anniversary tour of this Christmas classic highlighting the joy, kindness, love, and happiness of the winter season. Featuring a diverse international cast, this production has been staged in more than 140 North American cities, telling Tchaikovsky’s famed tale through breathtaking ballet.

Film

Silver screens across the county are glowing once again. Why not get in on the action with one of these celluloid gems?

Napoleon Dynamite

Sept 9; Tarrytown Music Hall

What once seemed like an incredibly quirky and overwhelmingly strange indie flick has become a cult classic. This screening of the 2004 film, about an awkward teen just trying to fit in with his unusual family and hostile schoolmates, will be followed by a freewheeling discussion with the film’s star, Jon Heder, who portrayed the title character, as well as costars Efren Ramirez and Jon Gries.

Love With the Proper Stranger

Sept 28; Jacob Burns Film Center

This five-time Academy Award-nominated romantic comedy stars Natalie Wood as an innocent salesgirl who finds solace in the arms of a charismatic jazz musician, played by Steve McQueen. When she becomes pregnant, Wood’s character must decide between the callow man her family wants her to marry and the noncommittal musician.

The Picture House German Film Festival

Oct 21–23; The Picture House

Sponsored by the Westchester Community Foundation, this annual film fest presented by The Picture House Regional Film Center shines a spotlight on both acclaimed and underappreciated works of German cinema. While The Picture House has not yet released the festival’s lineup, in past years they have screened such celebrated films as When Hitler Stole Pink Rabbit and Curveball.

The Rocky Horror Picture Show

Oct 30 & 31, The Picture House; Oct 29, Paramount Hudson Valley

Theatre Like any truly iconic holiday flick, The Rocky Horror Picture Show is screening at multiple area theaters. Even those with no interest in kooky musicals have likely heard of this trip through the strange world of Tim Curry’s Dr. Frank-N-Furter, who welcomes two eminently confused newlyweds to his laboratory.

Theater

To go out or not to go out? The answer is easy if you’re heading to one of these prime plays.

The Prom

Oct 7–23; White Plains Performing Arts Center

This musical comedy about a group of big-time Broadway stars who travel to Indiana on a mission to help a student banned from bringing her girlfriend to prom made a splash when it ran on the Great White Way and as a popular 2020 Netflix film. Now, local audiences can enjoy the sidesplitting plot and high-energy songs as it brings into focus just how important love and acceptance are, no matter where you call home.

My Sinatra

Oct 2; The Ridgefield Playhouse

The concert version of Cary Hoffman’s acclaimed Off-Broadway show presents one man’s journey through the songs of Frank Sinatra, who had an outsize impact on Hoffman’s life and career. Sung amid biographical musings and stirring stories, this one-man show includes more than 20 hits by Ol’ Blue Eyes interwoven with tales of Hoffman’s own childhood growing up fatherless.

Comedy

Get your laugh on at any one of these sidesplitting standup acts.

Kevin Nealon

Sept 30; Paramount Hudson Valley Theater

This beloved SNL alum is also a SAG- and Emmy-nominated actor, author, and comedian perhaps best known for his memorable turn on the hit Showtime series Weeds. Nealon, who has appeared in feature films like The Wedding Singer, Happy Gilmore, and Anger Management, recently resurfaced, starring on the CBS comedy show Man With a Plan and hosting his own YouTube series, Hiking With Kevin.

Paula Poundstone

Oct 21; Tarrytown Music Hall

From making merry on NPR’s hit quiz show Wait Wait… Don’t Tell Me and penning best-selling books to voice work on the Academy Award-winning film Inside Out, Paula Poundstone remains one of the hardest working women in comedy. Now, the Emmy Award-winning jokester and one of Comedy Central’s 100 Greatest Standups of All Time will be taking the standup stage this fall in Tarrytown.

Tracy Morgan

Oct 27; Paramount Hudson Valley Theater

This acclaimed funnyman made a name for himself as a long-running cast member on Saturday Night Live before earning widespread fame as befuddled rapper Tracy Jordan on the NBC sitcom 30Rock. Now, the star of the Emmy-nominated sitcom The Last O.G. is back on the standup stage for a night of unruly humor.

Kevin James

Oct 22; The Palace Theatre

Paul Blart: Mall Cop star Kevin James became a household name as Doug Heffernan on the hit sitcom King of Queens, for which he received a Primetime Emmy nomination in 2008. With roles in the feature films Pixels, Hitch, I Now Pronounce you Chuck & Larry, and Sandy Wexler, as well as voice work in Hotel Transylvania and Monster House, James is making his way to the region for some serious laughs.

Kevin James

Kevin James Oct 22; Palace Theatre. Kevin James photo by Tom Caltabiano/ Courtesy of the Palace Theatre.

Art

Experience some extraordinary exhibitions here in Westchester.

David Shaw: Last Steps

Sept 9–Apr 23, 2023; Aldrich Contemporary Art Museum

Brooklyn-based artist David Shaw explores technology, consciousness, nature, and the indistinct boundaries that divide them all in this striking installation as part of the Aldrich’s Main Street Sculpture Program. Consisting of a stepladder that seems to be in the process of both generation and decomposition, the sculpture shimmers with gleams of light peeking through a moss-like growth that obscures its surface. According to Shaw, the piece alludes to humanity’s misguided desire for progress and the constant hope of rebuilding and healing what has been broken.

Susan Wortman: Winged Women

Oct 1–31; Clay Art Center

After a devastating breast cancer diagnosis, CAC artist Susan Wortman began this series of hand-built paperclay sculptures to heal from a mastectomy and the psychological changes wrought by her disease. Representing health, strength, and hope, the 50 sculptures of Wortman’s Winged Women series serve as stirring symbols of the way one can triumph over adversity. Half the proceeds of each piece will be donated to the Westchester-based Cancer Support Team, a nonprofit organization that provides in-home services, social work, and nursing to cancer patients and their families.

The Family Portrait Exhibition

Sept 1 – Oct 15; Clay Art Center

What does it mean to be the member of a family, and how is identity formed through our respective kin? Clay Art Center’s annual Call for Entry Exhibit asks these potent questions as it explores the imagery, historical significance, systems, and metaphors of the family in contemporary culture and society. Curated by Kukuli Velarde, the show features artists like Sara Torgison and Jane Neuss Cohen creating functional and nonfunctional ceramic works investigating exactly what family means to them.

clay art

The Family Portrait Exhibition, Sept 1–Oct 15; Clay Art Center. The Family Portrait by Jane Neuss Cohen Thank The Lordy Loo/ Courtesy of The Clay Art Center.

Ultralight Beam

Sept 15–Oct 30; Pelham Art Center

Want to experience an exhibition tailor-made to expand your consciousness? For all those with a penchant for the trippy, this unique exhibit on show at Pelham Art Center features the work of several artists employing various media to explore spiritual and transcendental realms. The selected artists employ various forms of spirituality, visionary methods, religion, or metaphysics to create works featuring surrealism, abstraction, religious iconography, and other mind-bending aspects beyond easy classification.

art

Sarah Sanders Oracle/ Courtesy of Pelham Art Center.

The Social Fabric: Common Threads and Uncommon Vision

Oct 12–Jan 23; ArtsWestchester

Challenging preconceived notions of craft and social hierarchy, this forward-thinking exhibition on show at ArtsWestchester’s White Plains gallery uses fabric, textiles, and fiber art to spark a conversation about what it means to be an artist and who gets to be one. Featuring recent work and site-responsive commissions by New York-area artists, including Natalie Baxter, Jill Parry, Anthony Akinbola, and Lina Puerta, The Social Fabric takes up issues of climate change, identity, consumerism, history, and language. The powerful exhibition will also be accompanied by several public programs, featuring workshops, curator- and artist-led talks, and tours.

Hatching Color

Sept 9—Dec 18; KinoSaito Arts Center

This colorful exhibition on show throughout the fall comprises a host of paintings and drawings by KinoSaito Arts Center founder and famed abstract artist Kikuo Saito, who is known for his striking color fields and use of raw canvas. Saito’s wife, Mikiko Ino, served as curator for this touching tribute to the work of her late husband, gathering a host of pieces that have never before been exhibited. It all amounts to a master class in both abstract art and enduring devotion.

Related: Westchester’s Artistic Venues Are Hubs for Creativity and Culture

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