The Headless Horseman's Calendar

Tarrytown & Sleepy Hollow, NY

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

November

(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 6 (Thurs) Tarrytown Music Hall 8pm

Leslie Jones: Live

Leslie Jones is a three-time Primetime Emmy Award nominee as well as a Writer’s Guild Award and NAACP Award nominee for her work on SATURDAY NIGHT LIVE. She has also been honored as one of Time Magazine’s 100 Most Influential People. Jones recently wrapped production on season two of the HBO Max series OUR FLAG MEANS DEATH. The week of January 17th, 2023, Jones kicked off a new era of THE DAILY SHOW as the program's first guest host.

Nov 7 (Fri) Tarrytown Music Hall 8pm

Colin Hay

We are thrilled to welcome Colin Hay back in support of his new album Now and the Evermore. Colin first came to international fame with seminal ’80s hitmakers Men At Work. While the band would reach the heights of stardom—they took home a GRAMMY Award for Best New Artist and sold more than 30 million records worldwide on the strength of #1 singles like “Who Can It Be Now?” and “Down Under”—by 1985, they’d called it quits and gone their separate ways.

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!

Nov 8 (Sat) Tarrytown Music Hall 7 & 9:30pm

Jimmy Carr: Laughs Funny

If you like fast-paced, edgy one-liners then get ready to be happy. Jimmy Carr is going back on tour with his brand-new show ‘Jimmy Carr: Laughs Funny’.
Jimmy tells jokes, and jokes are like magnets. Jokes attract people, but they can also repel. Some people are repelled by Jimmy's dark brand of comedy. This show is not for them. But if it's the kind of thing you like, then this is the kind of thing you’ll like.

One of the biggest-selling comedy acts in the world, Jimmy consistently performs stand-up to sell-out crowds across the globe. At the latest count he has taken tour shows to over forty different countries and his last world tour, Terribly Funny, sold over 1.2 million tickets globally. Jimmy Carr: Laughs Funny will extend his reach even further and marks the first time this record-breaking comedian has toured in arenas in the UK and Ireland.

Nov 9 (Sun) Tarrytown Music Hall 3pm

Westchester Symphonic Winds - "Sonic Journeys"

Our new season of fine music for wind ensemble will kick off with a grand tour of Italy in our concert, “Sonic Journeys.” We will bring the majestic tone poem The Pines of Rome by Ottorino Respighi to life, taking you from the ancient Appian Way to the heart of the city’s gardens.
This concert will feature Schilke Trumpet Performing Artist, Morris Northcutt, who will dazzle you with a diverse set of works for flugelhorn, cornet, and trumpet. We’ll also be joined by Dr. Brian Cardany from the University of Rhode Island, who will conduct Urban Light by James M. David, along with apprentice conductor Katherine Filatov, leading Solas Ane by Samuel Hazo. The program will begin with the captivating Intrada by Steve Cohen.

Nov 9 (Sun) Tarrytown Music Hall 7:30pm

Film Series: Citizen Kane (11/9/25)

Classic films in a classic venue.
Following the death of publishing tycoon Charles Foster Kane, reporters scramble to uncover the meaning of his final utterance: 'Rosebud.'

Runtime: 119 Minutes. Directed by and starring Orson Welles

(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 11 (Tues) Tarrytown Music Hall 5pm

Junior Theater Production 2025: Shrek Jr

Presented by The Music Hall Academy

Performed by 3rd-8th graders. 
Directed and choreographed by Broadway’s Lauryn Ciardullo

(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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