The Headless Horseman's Calendar

Tarrytown & Sleepy Hollow, NY

Also check out our list of entertaining things to do happening all the time

October

Oct 14 (Tues) Tarrytown Music Hall 8pm

Ghost Tours of The Music Hall

Step into the eerie excitement of the Tarrytown Music Hall's ghost tours, where Master Storyteller Jonathan Kruk brings history and haunting tales to life! Explore the historic lore and discover the spirits lingering in this magnificent 1885 building, once a playground for Millionaires' Colony families like the Rockefellers and Vanderbilts. As you traverse its halls and learn about its storied past – from grand balls to wartime struggles – you'll uncover why some souls may have chosen to never leave. The Tarrytown Music Hall is an official site of the Haunted History Trail of New York State, and paranormal investigators have detected intriguing paranormal activity here. Get ready for a captivating and fun journey into the spooky side of history!

(Every Tues) Trivia Night 7pm at The Tapp (A fun local bar)

Free to Play! 1st & 2nd Place teams win gift certificates.

Oct 15 (Wed) Tarrytown Music Hall 8 pm

Ghost Tours of The Music Hall

Step into the eerie excitement of the Tarrytown Music Hall's ghost tours, where Master Storyteller Jonathan Kruk brings history and haunting tales to life! Explore the historic lore and discover the spirits lingering in this magnificent 1885 building, once a playground for Millionaires' Colony families like the Rockefellers and Vanderbilts. As you traverse its halls and learn about its storied past – from grand balls to wartime struggles – you'll uncover why some souls may have chosen to never leave. The Tarrytown Music Hall is an official site of the Haunted History Trail of New York State, and paranormal investigators have detected intriguing paranormal activity here. Get ready for a captivating and fun journey into the spooky side of history!

Oct 16 (Thurs) Tarrytown Music Hall 8pm

Pink Martini All Stars

Now in its 31st year, the unstoppable engine of joy that is Pink Martini continues to bring founder Thomas Lauderdale’s mission of multi-cultural connection and inclusion to concert stages on six continents. Presenting a mélange of catchy old-fashioned pop, global color, foot-tapping big band sound, and Hollywood glamour, Oregon’s most famous “little orchestra” performs music intended to appeal to everyone, regardless of age or background. Performing with a number of iconic voices including the band’s first lead singer China Forbes, NPR’s dashing Ari Shapiro, the soulful Edna Vazquez, America’s Got Talent finalist Jimmie Herrod, and international singing sensation Meow Meow, the “little orchestra” has played on legendary concert stages around the world, including the Hollywood Bowl, Carnegie Hall, the Sydney Opera House, Royal Albert Hall in London, and Bercy Arena in Paris.

(Every Thurs) Karaoke 8pm at The Tapp (A fun local bar)

Every Thursday we sing! Karaoke starts at 8 pm with a classic ice breaker. Warm up then choose your favorites from thousands of songs.

Oct 17 (Fri) Tarrytown Music Hall 8pm

Marty Stuart and His Fabulous Superlatives

An American country and bluegrass music singer, songwriter, and musician. Active since 1968, Stuart initially toured with Lester Flatt, and then in Johnny Cash's road band before beginning work as a solo artist in the early 1980s.

Oct 17 (Fri) Sleepy Hollow 8 pm

Sleepy Hollow Haunted Hayrides

Climb aboard Sleepy Hollow's legendary Haunted Hayride for a terrifying trip into the heart of the Headless Horseman's realm. As your hay wagon clatters down the Albany Post Road, you'll retrace Ichabod Crane's frantic escape, passing the Old Dutch Church before slipping through iron gates and into the dark woods of the Hollow.
Suddenly, shrieks and the thunder of hoofbeats echo around you, and you realize you're not alone. This is your chance to face the legendary horseman himself and see if you can keep your head! After your hair-raising ride, you can calm your nerves at a free block party on Beekman Avenue, which features live music, entertainment, and food.
The hayride departs from the Sleepy Hollow Village Hall, located at 28 Beekman Avenue. Tickets are sold exclusively online at the Village of Sleepy Hollow's website, sleepyhollowny.gov

Oct 18 (Sat) Tarrytown Music Hall 1pm

Spooky (but not too) Scary Stories

What makes kids Happy for Halloween? SPOOKY (But not too) SCARY STORIES!
Told by Legendary Storyteller, Jonathan Kruk at the Tarrytown Music Hall. Frightful fun with tales of the The Witch’s Surprise, Rolly-Head, the Haunted Hand, with live eerie music, and Jumpstarts! Jonathan Kruk is renowned for telling tales of the headless horseman and finger fables for kids. He has been featured on The Today Show, CBS Sunday Morning, and The Travel Channel.

Oct 18 (Sat) Tarrytown Music Hall 6pm & 9pm

Eric D'Alessandro

A charismatic New Yorker with an unfiltered sense of humor, a camera, and a knack for storytelling, has etched his name into the hearts of comedy lovers across the nation. His unique comedic style, infused with his Italian - American heritage, spins raw, relatable narratives that resonate with the everyday American
From his early beginnings on YouTube, Eric has steadily crafted a diverse portfolio of work that includes engaging sketches, spot-on celebrity impressions, and comedic covers of popular songs. His authentic characters, notably "Maria Marie," have garnered widespread acclaim, demonstrating Eric's ability to create content that both entertains and connects.

Oct 19 (Sun) Tarrytown Music Hall 1pm

The Very Hungry Caterpillar Interactive Show

The Very Hungry Caterpillar Interactive Show invites young audiences to embark on a captivating journey through the pages of the beloved Eric Carle books. As the enchanting tales come to life on stage, children will be immersed in the world of vibrant colors, well known characters, and wonderful storytelling. Through the magic of live theater, this interactive experience sparks the imagination, encouraging children to actively engage with the stories through call and response activities, encouraging them to count, identify colors and even participate in simple reading exercises. The gentle pace of the show and the cheerful storytelling create a safe and enjoyable environment, making it an ideal introduction to the wonders of the theatrical arts for little ones. By tapping into their boundless imagination, fostering a sense of discovery, and eliciting joyful laughter, The Very Hungry Caterpillar Interactive Show promises to be an unforgettable and educational adventure for children’s first theatrical encounter.

Oct 19 (Sun) Tarrytown Music Hall 7:30pm

Film Series: Alfred Hitchcock's Psycho

Classic films in a classic venue.
A secretary on the run for embezzlement takes refuge at a secluded California motel owned by a repressed man and his overbearing mother. Runtime: 109 Minutes. Directed by Alfred Hitchcock. Starring Anthony Perkins, Janet Leigh, Vera Miles.

Oct 20 (Mon) Tarrytown Music Hall 10:30pm

Ghost Tours of The Music Hall

Step into the eerie excitement of the Tarrytown Music Hall's ghost tours, where Master Storyteller Jonathan Kruk brings history and haunting tales to life! Explore the historic lore and discover the spirits lingering in this magnificent 1885 building, once a playground for Millionaires' Colony families like the Rockefellers and Vanderbilts. As you traverse its halls and learn about its storied past – from grand balls to wartime struggles – you'll uncover why some souls may have chosen to never leave. The Tarrytown Music Hall is an official site of the Haunted History Trail of New York State, and paranormal investigators have detected intriguing paranormal activity here. Get ready for a captivating and fun journey into the spooky side of history!

(Every Mon) Game Night 5pm-Mid at The Tapp (A fun local bar)

Come watch Monday Night sports with us or grab one of our board games and have some fun. Have a different one in mind? Bring your own!

Oct 21 (Tues) Tarrytown Music Hall 10:30pm

Ghost Tours of The Music Hall

Step into the eerie excitement of the Tarrytown Music Hall's ghost tours, where Master Storyteller Jonathan Kruk brings history and haunting tales to life! Explore the historic lore and discover the spirits lingering in this magnificent 1885 building, once a playground for Millionaires' Colony families like the Rockefellers and Vanderbilts. As you traverse its halls and learn about its storied past – from grand balls to wartime struggles – you'll uncover why some souls may have chosen to never leave. The Tarrytown Music Hall is an official site of the Haunted History Trail of New York State, and paranormal investigators have detected intriguing paranormal activity here. Get ready for a captivating and fun journey into the spooky side of history!

(Every Tues) Trivia Night 7pm at The Tapp (A fun local bar)

Free to Play! 1st & 2nd Place teams win gift certificates.

Oct 22 (Wed) Tarrytown Music Hall 10:30pm

Ghost Tours of The Music Hall

Step into the eerie excitement of the Tarrytown Music Hall's ghost tours, where Master Storyteller Jonathan Kruk brings history and haunting tales to life! Explore the historic lore and discover the spirits lingering in this magnificent 1885 building, once a playground for Millionaires' Colony families like the Rockefellers and Vanderbilts. As you traverse its halls and learn about its storied past – from grand balls to wartime struggles – you'll uncover why some souls may have chosen to never leave. The Tarrytown Music Hall is an official site of the Haunted History Trail of New York State, and paranormal investigators have detected intriguing paranormal activity here. Get ready for a captivating and fun journey into the spooky side of history!

Oct 23 (Thurs) Tarrytown Music Hall 11am & 12pm

Ghost Tours of The Music Hall

Step into the eerie excitement of the Tarrytown Music Hall's ghost tours, where Master Storyteller Jonathan Kruk brings history and haunting tales to life! Explore the historic lore and discover the spirits lingering in this magnificent 1885 building, once a playground for Millionaires' Colony families like the Rockefellers and Vanderbilts. As you traverse its halls and learn about its storied past – from grand balls to wartime struggles – you'll uncover why some souls may have chosen to never leave. The Tarrytown Music Hall is an official site of the Haunted History Trail of New York State, and paranormal investigators have detected intriguing paranormal activity here. Get ready for a captivating and fun journey into the spooky side of history!

Oct 23 (Thurs) Tarrytown Music Hall 7pm

Ride the Cyclone School Edition

Presented by The Music Hall Academy
Ride The Cyclone is a quirky, darkly comedic musical by Jacob Richmond and Brooke Marshall about six Canadian high school choir students who pass away in a roller coaster accident, only to find themselves in a limbo-like space where a mechanical fortune teller offers one of them a chance to return to life. Each student tells their story to prove why they deserve to be resurrected, leading to a varied and exciting musical score and a poignant exploration of life, death and the search for meaning. The show premiered in 2008 and has since become a cult hit, praised for its originality, humor and diverse musical numbers. Directed and choreographed by Broadway’s Lauryn Ciardullo. Performed by 7-12th graders

(Every Thurs) Karaoke 8pm at The Tapp (A fun local bar)

Every Thursday we sing! Karaoke starts at 8 pm with a classic ice breaker. Warm up then choose your favorites from thousands of songs.

Oct 24 (Fri) Tarrytown Music Hall 8pm

Tommy Emmanuel CGP - Living In The Light Tour

We are thrilled to welcome the world renowned guitar player Tommy Emmanuel back to the Music Hall! Tommy has a Grammy Award, multiple ARIA Awards and countless accolades, but nothing means more to Tommy than the three letters Chet Atkins designated at the end of Tommy’s name: C.G.P. The title of Certified Guitar Player was the highest honor Atkins could bestow on another player – a signifier that the recipient had not only mastered the instrument but taken it to new vistas and become a guiding light for the next generation of pickers. Like Tommy, Chet had never gone to a university, and the C.G.P. was his version of a PHD or a Doctorate of the guitar. He gave the honor to Tommy and only five other handpicked players.

Oct 25 (Sat) Tarrytown Music Hall 11am

Ride the Cyclone School Edition

Presented by The Music Hall Academy
Ride The Cyclone is a quirky, darkly comedic musical by Jacob Richmond and Brooke Marshall about six Canadian high school choir students who pass away in a roller coaster accident, only to find themselves in a limbo-like space where a mechanical fortune teller offers one of them a chance to return to life. Each student tells their story to prove why they deserve to be resurrected, leading to a varied and exciting musical score and a poignant exploration of life, death and the search for meaning. The show premiered in 2008 and has since become a cult hit, praised for its originality, humor and diverse musical numbers. Directed and choreographed by Broadway’s Lauryn Ciardullo. Performed by 7-12th graders

Oct 25 (Sat) Tarrytown's Main St & Broadway

Pre festivities 12pm, Parade 5pm, Block Party follows parade

Tarrytown Halloween Parade & Bloc Party

Experience the ultimate Halloween party at the Tarrytown Halloween Parade!
Join thousands of costumed revelers as they descend on the spookiest towns in America for a frightfully fun block party. You'll witness everything from spectacularly decorated floats to marching bands, performers, and more, all with a pulse-pounding rhythm to get you into the Halloween spirit.
The spectacle culminates in a massive block party on Main Street, where DJs will spin spine-chilling tracks and live music will fill the air. You can grab a bite from local eateries and mingle with fellow Halloween enthusiasts, including the grandest marshall of all: the legendary Headless Horseman!
Parking is extremely limited, so consider taking the Metro-North Railroad or a Westchester County bus for the easiest access.

Oct 25 (Sat) Tarrytown Music Hall 9 pm

The Rocky Horror Picture Show

RESERVE YOUR SPECIAL AUDIENCE PARTICIPATION KIT WITH YOUR TICKETS! LIVE SHADOW CAST!
In this cult classic, sweethearts Brad (Barry Bostwick) and Janet (Susan Sarandon), stuck with a flat tire during a storm, discover the eerie mansion of Dr. Frank-N-Furter (Tim Curry), a transvestite scientist. As their innocence is lost, Brad and Janet meet a houseful of wild characters, including a rocking biker (Meat Loaf) and a creepy butler (Richard O'Brien). Through elaborate dances and rock songs, Frank-N-Furter unveils his latest creation: a muscular man named "Rocky.”
Step into the ultimate cult-classic experience!! The Hoopla County Players of Tarrytown Music Hall bring the wild, outrageous and unforgettable world of The Rocky Horror Picture Show to life with authentic costumes, iconic props, and all the campy chaos you crave. This isn’t just a screening- it’s a full-blown spectacle where the line between audience and cast disappears.
Sing it. Shout it. Throw it! From noise makers to toilet paper, every prop and every cue is here to make YOU part of the show. Whether you’re a seasoned “ creature of the night” or a first-time “time-warp traveler” you’ll be swept into a hilarious, theatrical night of audience participation, outrageous performances and pure cult cinema magic.

Oct 26 (Sun) Tarrytown Music Hall 11am & 1pm

Amy Bruni - Walking With Ghosts

An Afternoon of True Crime Hauntings

Join Paranormal Researcher, author and podcaster Amy Bruni as she takes you through an unforgettable afternoon of ghost stories that originated from real-life murders.
Was a man truly executed based on the testimony of a ghost? Is one ghostly voice the key to finally solving the Villisca Axe Murders? Is the basement of the post office that now stands where the HH Holmes murder castle once was as haunted as the postal workers there would have you believe? Hear these stories and more, as Amy takes you through an evening of hauntings and the true crime mysteries surrounding them. Before she even takes the stage, peruse her small museum of haunted artifacts and spiritualist memorabilia. And at the end of the night, get your chance to ask her anything. Like, “can a ghost really follow you home?”

Oct 26 (Sun) Tarrytown Music Hall 5pm

Joe Avati

Internationally renowned for his inimitable style Avati, who is Australian born with an Italian heritage, is one of the most significant and pivotal comedians of his generation who, undoubtedly, is directly responsible for the ethnic comedy circuit around the world today.
For the past 30 years Joe Avati’s routines about growing up with a culturally diverse background have gained him a cult following around the globe. Avati has also become the master of treading the very fine line of saying whatever everyone seems to think but no one dares to say whilst not resorting to the use of profanities or vulgar shock tactic routines and in doing so allowing audiences of all ages to attend his shows. He has a razor sharp wit and his observations are not only deadly accurate but extremely relatable to his growing international audiences. Joe Avati is, without doubt, one of the world’s most loved and successful comedians of his generation.

Oct 27 (Mon) Tarrytown Music Hall 9:30pm

Ghost Tours of The Music Hall

Step into the eerie excitement of the Tarrytown Music Hall's ghost tours, where Master Storyteller Jonathan Kruk brings history and haunting tales to life! Explore the historic lore and discover the spirits lingering in this magnificent 1885 building, once a playground for Millionaires' Colony families like the Rockefellers and Vanderbilts. As you traverse its halls and learn about its storied past – from grand balls to wartime struggles – you'll uncover why some souls may have chosen to never leave. The Tarrytown Music Hall is an official site of the Haunted History Trail of New York State, and paranormal investigators have detected intriguing paranormal activity here. Get ready for a captivating and fun journey into the spooky side of history!

(Every Mon) Game Night 5pm-Mid at The Tapp (A fun local bar)

Come watch Monday Night sports with us or grab one of our board games and have some fun. Have a different one in mind? Bring your own!

Oct 28 (Tues) Tarrytown Music Hall 9:30pm

Ghost Tours of The Music Hall

Step into the eerie excitement of the Tarrytown Music Hall's ghost tours, where Master Storyteller Jonathan Kruk brings history and haunting tales to life! Explore the historic lore and discover the spirits lingering in this magnificent 1885 building, once a playground for Millionaires' Colony families like the Rockefellers and Vanderbilts. As you traverse its halls and learn about its storied past – from grand balls to wartime struggles – you'll uncover why some souls may have chosen to never leave. The Tarrytown Music Hall is an official site of the Haunted History Trail of New York State, and paranormal investigators have detected intriguing paranormal activity here. Get ready for a captivating and fun journey into the spooky side of history!

(Every Tues) Trivia Night 7pm at The Tapp (A fun local bar)

Free to Play! 1st & 2nd Place teams win gift certificates.

Oct 29 (Wed) Tarrytown Music Hall 11am & 12pm

Ghost Tours of The Music Hall

Step into the eerie excitement of the Tarrytown Music Hall's ghost tours, where Master Storyteller Jonathan Kruk brings history and haunting tales to life! Explore the historic lore and discover the spirits lingering in this magnificent 1885 building, once a playground for Millionaires' Colony families like the Rockefellers and Vanderbilts. As you traverse its halls and learn about its storied past – from grand balls to wartime struggles – you'll uncover why some souls may have chosen to never leave. The Tarrytown Music Hall is an official site of the Haunted History Trail of New York State, and paranormal investigators have detected intriguing paranormal activity here. Get ready for a captivating and fun journey into the spooky side of history!

Oct 29 (Wed) Tarrytown Music Hall 7pm

Warren Miller's "Sno-ciety"

From the Scottish Highlands and the streets of Finland to the back bowls of Whitewater, BC and a local hill-turned-terrain park in downtown Denver, Warren Miller’s SNO-CIETY celebrates the spirit of winter—wherever you ride and however you connect to the snow and the community around it.
Through the lens of Olympians, urban riders, and local legends, we uncover what drives us to chase powder year after year. Featuring Judd Henkes’ double life between surf and snow, Britta Winans’ resilient season on the Freeride World Tour, the frenzy of the Saalbach World Championships, and a shared mountain spirit that stretches from Tuckerman Ravine to Cairngorms National Park, SNO-CIETY explores the many ways we connect on snow—and with each other.

Oct 30 (Thurs) Tarrytown Music Hall 7pm

Tarrytown The Musical

Step into Tarrytown — Adam Wachter’s hauntingly beautiful new musical that reimagines Washington Irving’s timeless legend with a contemporary, heart-stirring score.

For one night only, Broadway and television favorites Krysta Rodriguez (The Addams Family, First Date, Smash) and Andy Mientus (Les Miserables, Spring Awakening, The Flash) illuminate the historic stage of the Tarrytown Music Hall — just steps from where the legend was first told.

With romance, wit, and music that blends Broadway brilliance with folk-inspired melodies, Tarrytown is more than a ghost story — it’s a tale of love, longing, and the ties that echo across time.

An exclusive, star-studded event in Sleepy Hollow’s own backyard.

(Every Thurs) Karaoke 8pm at The Tapp (A fun local bar)

Every Thursday we sing! Karaoke starts at 8 pm with a classic ice breaker. Warm up then choose your favorites from thousands of songs.

Oct 31 (Fri) Halloween Madness!!

November

Nov 2 (Sun) Tarrytown Music Hall 7pm

Natalie Merchant with Erik Della Penna: Autumn Acoustic Tour

Over her 40-year career Natalie Merchant has earned a reputation for being a songwriter and recording artist of rare quality, a captivating stage performer, and a skilled producer. She has also distinguished herself as a social justice and environmental activist through her work with a wide- variety of non-profit organizations, and by creating documentary films and large-scale community arts projects.

Natalie began her musical career as the lead vocalist and lyricist of the pop music band 10,000 Maniacs in 1981 and released two platinum and four gold records with the group. She left the band in 1993 and has subsequently released nine albums as a solo artist with combined sales of seven million copies.

(Every Mon) Game Night 5pm-Mid at The Tapp (A fun local bar)

Come watch Monday Night sports with us or grab one of our board games and have some fun. Have a different one in mind? Bring your own!

Nov 4 (Tue) Tarrytown Music Hall 5pm

Ghost Tours of The Music Hall

Step into the eerie excitement of the Tarrytown Music Hall's ghost tours, where Master Storyteller Jonathan Kruk brings history and haunting tales to life! Explore the historic lore and discover the spirits lingering in this magnificent 1885 building, once a playground for Millionaires' Colony families like the Rockefellers and Vanderbilts. As you traverse its halls and learn about its storied past – from grand balls to wartime struggles – you'll uncover why some souls may have chosen to never leave. The Tarrytown Music Hall is an official site of the Haunted History Trail of New York State, and paranormal investigators have detected intriguing paranormal activity here. Get ready for a captivating and fun journey into the spooky side of history!

(Every Tues) Trivia Night 7pm at The Tapp (A fun local bar)

Free to Play! 1st & 2nd Place teams win gift certificates.

Nov 6 (Thurs) Tarrytown Music Hall 3 & 4pm

Ghost Tours of The Music Hall

Step into the eerie excitement of the Tarrytown Music Hall's ghost tours, where Master Storyteller Jonathan Kruk brings history and haunting tales to life! Explore the historic lore and discover the spirits lingering in this magnificent 1885 building, once a playground for Millionaires' Colony families like the Rockefellers and Vanderbilts. As you traverse its halls and learn about its storied past – from grand balls to wartime struggles – you'll uncover why some souls may have chosen to never leave. The Tarrytown Music Hall is an official site of the Haunted History Trail of New York State, and paranormal investigators have detected intriguing paranormal activity here. Get ready for a captivating and fun journey into the spooky side of history!

Nov 8 (Sat) Tarrytown Music Hall 2 & 3pm

Ghost Tours of The Music Hall

Step into the eerie excitement of the Tarrytown Music Hall's ghost tours, where Master Storyteller Jonathan Kruk brings history and haunting tales to life! Explore the historic lore and discover the spirits lingering in this magnificent 1885 building, once a playground for Millionaires' Colony families like the Rockefellers and Vanderbilts. As you traverse its halls and learn about its storied past – from grand balls to wartime struggles – you'll uncover why some souls may have chosen to never leave. The Tarrytown Music Hall is an official site of the Haunted History Trail of New York State, and paranormal investigators have detected intriguing paranormal activity here. Get ready for a captivating and fun journey into the spooky side of history!

(Every Mon) Game Night 5pm-Mid at The Tapp (A fun local bar)

Come watch Monday Night sports with us or grab one of our board games and have some fun. Have a different one in mind? Bring your own!

(Every Tues) Trivia Night 7pm at The Tapp (A fun local bar)

Free to Play! 1st & 2nd Place teams win gift certificates.

(Every Thurs) Karaoke 8pm at The Tapp (A fun local bar)

Every Thursday we sing! Karaoke starts at 8 pm with a classic ice breaker. Warm up then choose your favorites from thousands of songs.

 

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