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
(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
Oct 16 (Thurs) Tarrytown Music Hall 8pm
Pink Martini All Stars
(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
Oct 17 (Fri) Sleepy Hollow 8 pm
Sleepy Hollow Haunted Hayrides
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.
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
Oct 19 (Sun) Tarrytown Music Hall 1pm
The Very Hungry Caterpillar Interactive Show
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
(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
(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
Oct 23 (Thurs) Tarrytown Music Hall 11am & 12pm
Ghost Tours of The Music Hall
Oct 23 (Thurs) Tarrytown Music Hall 7pm
Ride the Cyclone School Edition
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
Oct 25 (Sat) Tarrytown Music Hall 11am
Ride the Cyclone School Edition
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
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!
Oct 25 (Sat) Tarrytown Music Hall 9 pm
The Rocky Horror Picture Show
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.”
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
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
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
(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
(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
Oct 29 (Wed) Tarrytown Music Hall 7pm
Warren Miller's "Sno-ciety"
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
(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
Nov 8 (Sat) Tarrytown Music Hall 2 & 3pm
Ghost Tours of The Music Hall
(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.