Tarrytown / Sleepy Hollow NY - Calendar of Things to Do

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.

Sep 24 (Wed) 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!

Sep 24 (Wed) Tarrytown Music Hall 7:30pm

Kevin James: Owls Don’t Walk

Kevin James began his career as a stand-up on the Long Island comedy scene. After being discovered at the 1996 Montreal Comedy Festival, he signed a network development deal to create his own sitcom.
The King of Queens, which premiered in 1998, ran for nine seasons on CBS with James starring and executive producing, and it garnered him an Emmy nomination for Outstanding Lead Actor in a Comedy Series. The show concluded its run in 2007 but continues to air daily in syndication across the country and around the world. James brought his stand-up act to TV with Sweat the Small Stuff, a one-hour special for Comedy Central.

(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.

Sep 28 (Sun) 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 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.

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 6 (Mon) Tarrytown Music Hall 7pm

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 7 (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 8 (Wed) Tarrytown Music Hall 11am

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 9 (Thurs) Tarrytown Music Hall 11am

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 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 10 (Fri) Tarrytown Music Hall 11am

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 11 (Sat) Tarrytown Music Hall 10am

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 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!

(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 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 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!

(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 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 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!

(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)

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 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!

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The Headless Horseman's Calendar