The Hottest Arts & Events Happening in Westchester This Fall

Stephen Hough. Nov 14, Caramoor Center for Music and the Arts. Photo by Sim Cannety-Clarke

From art shows to film screenings and music fests (and more), there are so many incredible things to do in the 914 all autumn long.

Undaunted by the pandemic and charged with momentum, Westchester’s cultural institutions have risen from the past year stronger than ever. With a fleet of reopened venues holding some of the most exciting, colorful, and innovative exhibitions and events the county has yet to see, this fall will be one to remember. Follow along as we round up all the fun festivals, musical performances, must-attend events, art exhibitions, theatrical productions, standup comedy acts, kids’ shows, and much more to be savored throughout the season.

Hot List

Looking for the cream of the crop of fall events? Try this list of the hottest events and exhibitions.

Lisa Loeb, fall events
Photo by Juan Patino

Lisa Loeb

Oct 14, The Emelin Theatre

Seems like her seminal hit “Stay” is still part of the zeitgeist, appearing in recent TV commercials (and our earworms). Why not see the star who wrote the tear-jerker when she drops by the Emelin this month?

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Alan Menken

Nov 6, The Ridgefield Playhouse

Do the animated films Aladdin, The Little Mermaid, and Beauty and the Beast ring a bell? If so, you can see the fellow who composed the songs for these Disney gems — and took home (to Westchester) more competitive Academy Awards than any living person — live onstage.


Oct 3–Jan 23, 2022, Katonah Museum of Art

Top-tier, in-person art exhibitions are back. Case in point: this exceptional show investigating the origins of American immigrants and enslaved peoples through works by lauded artists like Kara Walker and Dorothea Lange.


Sept 10, The Capitol Theatre

Catch the indie-rock pioneers known for influencing ’90s mainstays like Nirvana and Radiohead with hits like “Wave of Mutilation” and “Where Is My Mind” during this rare area show.


Oct 8–24, White Plains Performing Arts Center

The White Plains Performing Arts Center is back to doing what it does best, with the New York premiere of this lighthearted musical portrait of Andrew Lloyd Webber’s remarkable life.

fall events
Photo © Brigitte Lacombe

Fran Lebowitz

Nov 7, The Ridgefield Playhouse

While it may seem unlikely, New York-art-scene icon, Netflix series star, and culture-shifting essayist Fran Lebowitz will be taking the stage to discuss her life and work.

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Norm Macdonald

Nov 10, Tarrytown Music Hall

Need a laugh after the last year? You’re not alone. Luckily, the Saturday Night Live alum and costar of such films as Billy Madison and Funny People is making his way to the region this fall.

The Symphony of Westchester

Nov 13, Iona College

The Symphony of Westchester marks its triumphant return with this Mostly Mozart concert helmed by UMKC Concerto/Aria competition winner and acclaimed pianist Zheyu Jiang.

Kids’ Corner

Are the little ones getting a bit stir-crazy? Steer them toward one of these fun family events.

Rudolph the Red-Nosed Reindeer

Nov 27, The Palace Theatre

Holiday lovers of all ages are invited to see their favorite characters from the classic TV special during this music-filled stage show. Featuring Hermey the Misfit Elf, the Abominable Snow Monster, Santa Claus, and the titular reindeer, this heartwarming musical teaches kids that what makes us different can make us stronger.

imagination movers
Photo by Imagination Movers

Imagination Movers

Oct 9, Paramount Hudson Valley

This energetic alternative-rock band for young ones has come a long way from their New Orleans roots. A fixture on SiriusXM’s Kids Place Live!, this lauded, family-focused group has been featured on Good Morning America, The View, and NPR’s American Routes. Now, area families can see their interactive, fun-filled performances in person during this lighthearted Peekskill show that’s perfect for preschoolers.

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Wakanda4Ever Celebration

Sept 4, Luangisa African Gallery

Celebrate community and African culture during this Mount Vernon event perfect for the entire family. Inspired by the hit Disney film Black Panther and dedicated to illuminating the heritage of African Americans, this event stretching from 10 a.m. to 10 p.m. includes a Wakanda Fashion Show, honoring the life of actor Chadwick Boseman, a live African band, storytelling for children, crafts, a curated selection of home decor for sale, and Black Panther characters on hand.


From rock and pop to classical and jazz, here are our picks for some of the top acts to lend an ear to this fall.

Rock & Pop

Phil Lesh & Friends

Oct 11, 12, 13, 18, 19, 20; The Capitol Theatre

What a long, strange trip it’s been for the founding bassist of the Grateful Dead, Phil Lesh, who has had a major renaissance since founding the ultra-popular jam band that bears his name. In October, Lesh will spend six evenings in Port Chester, demonstrating why he remains an outsized force in rock more than half a century since he first took the stage.

fall events
Photo courtesy of The Capitol Theatre


Sept 10, The Capitol Theatre

Ask any music snob about the most influential indie-rock bands, and there’s a good chance they’ll mention these punk pioneers known for moody, infectious hits like “Here Comes Your Man” and “Debaser,” as well as their perpetually sold-out world tours.

Mary Chapin Carpenter, Marc Cohn & Shawn Colvin

Oct 10, Tarrytown Music Hall

Catch three incredibly talented musicians performing together for one evening during this show at Tarrytown Music Hall. The recipient of five Grammys and two CMA awards, Carpenter will be joined onstage by two other widely acclaimed Grammy winners: Colvin, known for her 1998 hit, “Sunny Came Home,” and “Walking in Memphis” singer Marc Cohn.

Lisa Loeb

Oct 14, Emelin Theatre

Will the Platinum-selling ultra-bop “Stay (I Missed You)” ever fade from playlists? When timeless pop star Lisa Loeb isn’t performing on Last Week Tonight with John Oliver or at the Tribeca Film Festival, she is acting in Netflix shows, like Sandy Wexler and TV Land’s Teachers. Embrace all that made the ’90s great, when the Grammy Award winner drops by the Emelin.

The Monkees Farewell Tour

Oct 20, Tarrytown Music Hall

The Monkees’ Michael Nesmith and Micky Dolenz are currently on a tear-filled farewell tour, marking 55 years as a band. Known for songs that helped define the ’60s, like “I’m a Believer” and “Last Train to Clarksville,” the duo’s performance will feature hits from throughout The Monkees’ storied career, all the way from their 1966 self-titled debut album to 2016’s Good Times.


Oct 27, The Capitol Theatre

Ah, the ’80s. If you’d like to relive all the big hair, wild looks, and iconic sounds of the day, take an evening out to see this British-American supergroup who have sold more than 80 million records and are known for radio-friendly ballads, like “Cold as Ice,” “Hot Blooded,” and “Juke Box Hero.”

Rosanne Cash

Nov 13, Tarrytown Music Hall

Catch this four-time Grammy Award winner boasting 21 top-40 hits and 11 chart-topping singles when she drops by Tarrytown Music Hall. Along with her 15 acclaimed studio albums, Cash is also the noted author of four books, including the bestselling memoir Composed.

Pat Benatar & Neil Giraldo

Sept 23, The Ridgefield Playhouse

If you still find yourself humming along to “Hit Me With Your Best Shot” or “Love Is a Battlefield,” you may want to drop by this rollicking rock show featuring a duo of musicians boasting a combined 19 top-40 hits and four consecutive Grammy wins, not to mention more than 30 million albums sold worldwide.

fall events
Photo by Amy Kerwin

Leo Kottke

Oct 17, Emelin Theatre

Having worked with names like Procol Harum and Violent Femmes, Grammy-nominated Leo Kottke is among the world’s foremost steel-string fingerstyle guitarists. This fall, area audiences have a chance to see the maestro in action when he takes the Mamaroneck stage for a performance of his unique style, which blends jazz, blues, folk, and rock.

Classical, Jazz & World Music

Taconic Opera

Oct 30, 31, Yorktown Stage

Experience this celebrated opera’s triumphant return with their first indoor, mainstage, fully orchestrated production since 2019. Celebrating its 24th season, the Taconic Opera will perform Puccini’s moving Manon Lescaut, with supertitles positioned above the stage so that those who do not speak Italian can follow along.

Evnin Rising Stars

Oct 31, Caramoor Center for Music and the Arts

Meet the next generation of great classical artists when violist Daniel Phillips and Caramoor guest artistic director and renowned cellist Marcy Rose perform chamber music masterworks alongside up-and-coming young artists they have mentored.

Stephen Hough. Nov 14, Caramoor Center for Music and the Arts. Photo by Sim Cannety-Clarke

Stephen Hough

Nov 14, Caramoor Center for Music and the Arts

Works by Schumann, Chopin, Rawsthorne, and Stephen Hough himself are on the menu when the lauded pianist, writer, and composer takes the stage in Caramoor’s attractive Music Room. The winner of the 1983 Naumberg International Piano Competition and an honorary member of London’s Royal Academy of Music, Hough presents a rare treat for fans of top-flight piano.

Symphony of Westchester

Nov 13, Iona College

The UMKC Concerto/Aria competition winner and lauded young pianist Zheyu Jiang leads the Symphony of Westchester in this Mostly Mozart performance featuring the maestro’s Overture: La finta Giardiniera and Piano Concerto no. 19, as well as Haydn’s Symphony no. 45.

fall events
Photo courtesy of Caramoor Center for Music and the Arts

Callisto Quartet

Nov 7, Caramoor Center for Music and the Arts

The Ernst Steifel residents at Caramoor present the world premiere of a new work by composer Nathaniel Heyder, as well as a selection of Beethoven and the Mendelssohn string quartet that helped inspire Heyder’s piece.


The Rise of Social Consciousness in the Arts of Mexico Since the Revolution

Sept 15, 2021–Dec 24; Neuberger Museum of Art

Mexico sustained a turbulent decade of revolution beginning in 1910 that forever changed its art and culture. Following the upheaval, painters, engravers, and photographers increasingly examined Mexican history, pre-Columbian art, traditional crafts, and daily scenes. This exhibition, featuring a host of works from the permanent collection of the Neuberger Museum of Art, chronicles this enormous ideological shift, as well as the outsized role modern Mexican artists played in shepherding creative change. The show includes several thought-provoking pieces by artists such as José Raúl Anguiano Valadez, Teresa Margolles, and Betsabeé Romero.


Oct 3, 2021–Jan 23, 2022; Katonah Museum of Art

Where did we come from? What constitutes our personal and shared cultural heritage? These questions and many others are proposed by this captivating exhibit at the Katonah Museum of Art that explores Americans’ varying origin stories. Focusing on a series of arrival moments, such as Ellis Island, the Pilgrims, and the Middle Passage, this wide-ranging exhibition will feature 50 works spanning the 16th century to the present day, by noted artists including Vanessa German, Titus Kaphar, Thuan Vu, and Kara Walker. Belonging, otherness, displacement, race, and resilience are all touched on in this multimedia show exploring how artists have explored the myths and narratives surrounding what it means to be American.

RESOLUTE: Native Nations Art in the Bruce Collection

Nov 6, 2021–Jan 31, 2022; The Bruce Museum

Native American artwork rarely gets its due, an issue being remedied by organizations like Greenwich’s Bruce Museum, which will be showcasing a panoply of significant objects from the institution’s Native Nations Collection. Providing never-before-exhibited information that has been verified by the museum, RESOLUTE sheds new light on the previously unattributed works that populate the show, including pieces by 19th-century Haida painter Tom Price and Navajo master silversmith Fred Peshlakai. The exhibition also marks a fruitful, ongoing collaboration between the museum and experts and elders from the Mashantucket Pequot tribe, the Mohegan Tantaquidgeon Museum, and other native peoples and organizations.

Karla Knight, Blue Navigator 2, 2021, flashe, acrylic marker, pencil, and embroidery on cotton. 68 x 50 inches. Courtesy of the artist
Karla Knight, Blue Navigator 2, 2021, flashe, acrylic marker, pencil, and embroidery on cotton. 68 x 50 inches. Courtesy of the artist

Karla Knight: Navigator

Oct 17, 2021–May 1, 2022; Aldrich Contemporary Art Museum

Scientific schematics, the occult, surrealism, Native American symbolism, and early-20th-century abstraction all combine in the pulsating, energetic work of Karla Knight. An artist whose oeuvre has spanned painting, photography, and drawing over a 40-year career, Navigator marks Knight’s first institutional solo show. The innovative exhibit will take the form of a focused survey that explores the development of the artist’s unique visual language through several paintings and works on paper, as well as an entirely new series of works on seed and grain bags that Knight refers to as “tapestries.”

Funky Fests

Those looking to get back into the swing of things with an all-out event can take their pick from this lineup of exceptional area festivals.

Emmet Cohen will be performing at JazzFest White Plains. Photo by Taili Song Roth
Emmet Cohen will be performing at JazzFest White Plains. Photo by Taili Song Roth

2021 JazzFest White Plains

Sept 9–12, Various Locations

Jazz lovers unite! This beloved annual fest presented by White Plains’ ArtsWestchester is back for the 2021 season with an in-person lineup composed of some impressive names. Celebrating its 10th year and taking place in various locations throughout the city, JazzFest features performances by 2019 American Pianists Award winner Emmet Cohen, noted saxophonist Erena Terakubo, and Samara Joy, winner of the 2019 Sarah Vaughan International Jazz Vocal Competition.

Armonk Outdoor Art Show

Sept 25–26; 205 Business Park Dr

Ranked among the best arts-and-crafts shows in America, this expansive outdoor event once again descends upon our region. Sporting a veritable tsunami of paintings, prints, sculptures, drawings, pastels, mixed media, photography, digital works, fashion, fine arts, and much more — all available for sale in an open-air environment that is friendly to family members of all ages.


Oct 15–17; Various Locations

Featuring a host of exhibitions, activities, and programs held at more than 40 venues throughout New Rochelle and Pelham, ArtsFest returns in top form this fall. Presented by New Rochelle’s Council on the Arts, the expansive event includes film screenings, artist workshops, dance performances, a free “Arts in Oktoberfest” gallery hop during which attendees can check out open studios, as well as a classic car show, a dance festival, and even spoken-word performances.

Fall Crafts at Lyndhurst

Sept 17–19; Lyndhurst

Craft shows come and go, but this autumn extravaganza at Tarrytown’s Lyndhurst really is something to crow about. With 300 artists filling the mansion’s expansive grounds, selling an eye-popping array of fall finery, from pottery to paintings and almost everything in between, this year’s event features plenty of exciting activities, including live music, gourmet food, craft demonstrations, kids’ activities, and tours of Lyndhurst.

The Great Jack O’Lantern Blaze

Sept 17–Nov 21; Van Cortlandt Manor

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 each fall. Featuring 7,000 hand-carved, illuminated jack-o’-lanterns in a dizzying array of forms — from a pumpkin carousel to a pumpkin planetarium — the fall event even boasts a Museum of Pumpkin Art, decked with gourds paying tribute to timeless paintings.


By Frank Roberts

JB Smoove

Nov 20, Paramount Hudson Valley Theater

Most know this lauded standup from his role as Leon in the hit HBO comedy series Curb Your Enthusiasm, but this multitalented entertainer has plenty more up his sleeve. Recently penning the Audie Award-nominated The Book of Leon: Philosophy of a Fool, based on his Curb character, Smoove has also appeared on the ABC comedy Fresh off the Boat, BET’s The Real Husbands of Hollywood, and the CBS series The Millers and Everybody Hates Chris. This fall, audiences can catch the Mr. Deeds and The Dictator star cracking wise in the flesh.

Norm Macdonald

Nov 10, Tarrytown Music Hall

After anchoring the Weekend Update desk on Saturday Night Live, this sharp-tongued standup star made his name in flicks like Billy Madison, Grown Ups, Funny People, and Deuce Bigalow: Male Gigolo, as well as spots in hit TV series, like Roseanne, My Name Is Earl, and The Drew Carry Show. This fall, the acclaimed comic will take the stage for a night of singular humor.

Jay Mohr

Oct 2, Paramount Hudson Valley Theater

If you don’t recognize actor, comedian, and bestselling author Jay Mohr from his years on Saturday Night Live, or perhaps from his roles in roughly 25 feature films, including Jerry Maguire and Pay It Forward, maybe you will know from his appearances on more than 50 different sitcoms and TV dramas. The author of his own memoir and a frequent contributor on several radio shows, Mohr is a multitalented funnyman well worth a watch.

Photo courtesy of Ridgefield Playhouse

Andrew Dice Clay

Sept 9, The Ridgefield Playhouse

The first comedian to sell out Madison Square Garden two nights in a row, Andrew Dice Clay remains one of standup’s most notorious names, boasting HBO and Showtime specials, as well as bestselling CDs and DVDs. With roles in films like Blue Jasmine and A Star Is Born, as well as two seasons of his own Showtime series, Dice, the comedy legend will take the Ridgefield stage in September for a night of his “lewd, rude, and crude” brand of humor.

Anthony Rodia

Oct 9, The Palace Theatre

Westchester’s own Anthony Rodia has been making his native county proud. Swiftly rising in the national comedy scene, Rodia has already amassed more than 700,000 social media followers and racked up in excess of 22 million YouTube views due to his approachable jokes and sold-out appearances at acclaimed comedy clubs across the country.


The October Storm

Oct 8–23, Whippoorwill Theatre, North Castle Public Library

Telling the tale of a troubled war veteran at odds with his building’s confident landlady and involved with her 16-year-old granddaughter, The October Storm marks the world premiere of Juilliard-trained playwright Joshua Allen’s newest work. Presented by The Hudson Stage Company and directed by New York-based actor and award-winning director Cezar Williams, the play presents a soulful portrait of a man lost in 1960s Chicago.


Oct 8–24, White Plains Performing Arts Center

Composer Andrew Lloyd Webber singlehandedly redefined modern musical theater with iconic works like Cats, Phantom of the Opera, Evita, and Jesus Christ Superstar. Local audiences can now celebrate the British-born genius during the New York premiere of this lighthearted musical portrait following Webber’s decades-long career, from his bohemian youth and quirky family life to his days in the spotlight, crafting some of Broadway’s most celebrated works.

FRIENDS! The Musical Parody

Nov 12, Tarrytown Music Hall

If you find yourself pining for the days of Ross and Rachel, FRIENDS! The Musical Parody just might be your ticket back to ’90s-era bliss. This comedic musical onstage at Tarrytown Music Hall lets audiences step back into Central Perk alongside their favorite band of wacky, 20-something buddies, in a production that lovingly pokes fun at the megahit sitcom while celebrating everything that made it great.

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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