The Headless Horseman's Calendar
Tarrytown & Sleepy Hollow, NY
A calendar of upcoming events and things to do.
Also check out our list of entertaining things to do happening all the time
June 2 (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. Choose from Chess, Checkers, Connect 4, Guess Who, Trivia, Cards Against Humanity and more. Have a different one in mind? Bring your own!
June 3 (Tues) Trivia Night 7pm at The Tapp (A fun local bar)
Free to Play! 1st & 2nd Place teams win gift certificates.
June 4 (Wed) Tarrytown Music Hall 7:30pm
Marc Roberge of O.A.R.
As frontman for multi-platinum-selling alt-rock band O.A.R., Marc Roberge has performed for sold-out crowds at many of the world’s most iconic venues and helped to build a singularly devoted fanbase that spans the entire globe.
With the band now on their tenth studio album (2022’s The Arcade), the New York City-based singer/songwriter/guitarist has also established a dynamic career as a solo artist over the past decade. In a departure from the unbridled energy of O.A.R.’s live show, Roberge’s solo tours find him taking the stage at more intimate theaters and delivering stripped-back renditions of O.A.R. fan favorites, along with a carefully curated selection of covers.
June 5 (Thurs) Tarrytown Music Hall 8pm
Chris Botti
Chris Botti has been one of the most popular instrumentalists in the world for nearly three decades. Coming to prominence with the 2001 recording of his Night Sessions CD, Botti established a reputation as a versatile musician in both jazz and pop music for his ability to fuse both styles together. Chris Botti has thoroughly established himself as one of the important, innovative figures of the contemporary music world. Three of his albums have also reached the #1 position on the Billboard jazz albums chart.
June 5 (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.
June 6 (Fri) Tarrytown Music Hall 6:30pm
MK Dance On Hudson 2025 Showcase
MK Dance On Hudson is thrilled to present our 2025 Showcase on June 6, 7 & 8. Join us in supporting and celebrating all of our students who have worked so hard this year. Sit back, relax and enjoy as our students, ages 3-18yrs old, showcase their dancing in Ballet, Pointe, Modern, Contemporary, Jazz, Hip Hop, Musical Theatre, Tap, Creative Movement and more!
June 7 (Sat) Tarrytown Music Hall 4pm
MK Dance On Hudson 2025 Showcase
MK Dance On Hudson is thrilled to present our 2025 Showcase on June 6, 7 & 8. Join us in supporting and celebrating all of our students who have worked so hard this year. Sit back, relax and enjoy as our students, ages 3-18yrs old, showcase their dancing in Ballet, Pointe, Modern, Contemporary, Jazz, Hip Hop, Musical Theatre, Tap, Creative Movement and more!
June 7 (Sat) Sleepy Hollow Music Festival Time tba
Enjoy a full day of world class live music, award winning food and drink, and engaging kids entertainment. All in a beautiful setting on the banks of the Hudson River.
June 8 (Sun) Tarrytown Open Streets 11am-3
Celebrate Gay Pride in Tarrytown with the Open Streets event.
June 8 (Sun) Tarrytown Music Hall 10am
MK Dance On Hudson 2025 Showcase
MK Dance On Hudson is thrilled to present our 2025 Showcase on June 6, 7 & 8. Join us in supporting and celebrating all of our students who have worked so hard this year. Sit back, relax and enjoy as our students, ages 3-18yrs old, showcase their dancing in Ballet, Pointe, Modern, Contemporary, Jazz, Hip Hop, Musical Theatre, Tap, Creative Movement and more!
June 9 (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. Choose from Chess, Checkers, Connect 4, Guess Who, Trivia, Cards Against Humanity and more. Have a different one in mind? Bring your own!
June 10 (Tues) Trivia Night 7pm at The Tapp (A fun local bar)
Free to Play! 1st & 2nd Place teams win gift certificates.
June 12 (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.
June 16 (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. Choose from Chess, Checkers, Connect 4, Guess Who, Trivia, Cards Against Humanity and more. Have a different one in mind? Bring your own!
June 17 (Tues) Trivia Night 7pm at The Tapp (A fun local bar)
Free to Play! 1st & 2nd Place teams win gift certificates.
June 19 (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.
June 23 (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. Choose from Chess, Checkers, Connect 4, Guess Who, Trivia, Cards Against Humanity and more. Have a different one in mind? Bring your own!
June 24 (Tues) Trivia Night 7pm at The Tapp (A fun local bar)
Free to Play! 1st & 2nd Place teams win gift certificates.
June 26 (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.
June 26 (Thurs) Tarrytown Summer Concerts 7-9pm at Pierson Park
The Saints
The Tarrytown Summer Concert Series is a lively community tradition that brings music, dancing, and fun to the heart of the village! Set against the scenic backdrop of the Hudson River, families and friends gather each week to enjoy live performances from local bands, food vendors, and a festive, laid-back atmosphere that captures the joy of summer. (June 26-August 28 from 7pm to 9pm)
June 30 (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. Choose from Chess, Checkers, Connect 4, Guess Who, Trivia, Cards Against Humanity and more. Have a different one in mind? Bring your own!
July
July 1 (Tues) Trivia Night 7pm at The Tapp (A fun local bar)
Free to Play! 1st & 2nd Place teams win gift certificates.
July 3 (Thurs) Tarrytown Summer Concerts 7-9pm at Pierson Park
NuPhamlee Soul
The Tarrytown Summer Concert Series is a lively community tradition that brings music, dancing, and fun to the heart of the village! Set against the scenic backdrop of the Hudson River, families and friends gather each week to enjoy live performances from local bands, food vendors, and a festive, laid-back atmosphere that captures the joy of summer. (June 26-August 28 from 7pm to 9pm)
July 3 (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.
July 4 (Fri) Tarrytown Summer Concerts 7-9pm at Pierson Park
Kickstart Charlie
The Tarrytown Summer Concert Series is a lively community tradition that brings music, dancing, and fun to the heart of the village! Set against the scenic backdrop of the Hudson River, families and friends gather each week to enjoy live performances from local bands, food vendors, and a festive, laid-back atmosphere that captures the joy of summer. (June 26-August 28 from 7pm to 9pm)
July 7 (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. Choose from Chess, Checkers, Connect 4, Guess Who, Trivia, Cards Against Humanity and more. Have a different one in mind? Bring your own!
July 8 (Tues) Trivia Night 7pm at The Tapp (A fun local bar)
Free to Play! 1st & 2nd Place teams win gift certificates.
July 10 (Thurs) Tarrytown Summer Concerts 7-9pm at Pierson Park
Grateful Bro
The Tarrytown Summer Concert Series is a lively community tradition that brings music, dancing, and fun to the heart of the village! Set against the scenic backdrop of the Hudson River, families and friends gather each week to enjoy live performances from local bands, food vendors, and a festive, laid-back atmosphere that captures the joy of summer. (June 26-August 28 from 7pm to 9pm)
July 10 (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.
July 14 (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. Choose from Chess, Checkers, Connect 4, Guess Who, Trivia, Cards Against Humanity and more. Have a different one in mind? Bring your own!
July 15 (Tues) Trivia Night 7pm at The Tapp (A fun local bar)
Free to Play! 1st & 2nd Place teams win gift certificates.
July 17 (Thurs) Tarrytown Summer Concerts 7-9pm at Pierson Park
Tangled Vine
The Tarrytown Summer Concert Series is a lively community tradition that brings music, dancing, and fun to the heart of the village! Set against the scenic backdrop of the Hudson River, families and friends gather each week to enjoy live performances from local bands, food vendors, and a festive, laid-back atmosphere that captures the joy of summer. (June 26-August 28 from 7pm to 9pm)
July 17 (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.
(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. Choose from Chess, Checkers, Connect 4, Guess Who, Trivia, Cards Against Humanity and more. 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.
July 24 (Thurs) Tarrytown Summer Concerts 7-9pm at Pierson Park
The Leftovers
The Tarrytown Summer Concert Series is a lively community tradition that brings music, dancing, and fun to the heart of the village! Set against the scenic backdrop of the Hudson River, families and friends gather each week to enjoy live performances from local bands, food vendors, and a festive, laid-back atmosphere that captures the joy of summer. (June 26-August 28 from 7pm to 9pm)
(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.
(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. Choose from Chess, Checkers, Connect 4, Guess Who, Trivia, Cards Against Humanity and more. 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.
July 31 (Thurs) Tarrytown Summer Concerts 7-9pm at Pierson Park
Frankie Sands
The Tarrytown Summer Concert Series is a lively community tradition that brings music, dancing, and fun to the heart of the village! Set against the scenic backdrop of the Hudson River, families and friends gather each week to enjoy live performances from local bands, food vendors, and a festive, laid-back atmosphere that captures the joy of summer. (June 26-August 28 from 7pm to 9pm)
August
(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.
(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. Choose from Chess, Checkers, Connect 4, Guess Who, Trivia, Cards Against Humanity and more. 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.
Aug 7 (Thurs) Tarrytown Summer Concerts 7-9pm at Pierson Park
Funk & Disorderly
The Tarrytown Summer Concert Series is a lively community tradition that brings music, dancing, and fun to the heart of the village! Set against the scenic backdrop of the Hudson River, families and friends gather each week to enjoy live performances from local bands, food vendors, and a festive, laid-back atmosphere that captures the joy of summer. (June 26-August 28 from 7pm to 9pm)
(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.
(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. Choose from Chess, Checkers, Connect 4, Guess Who, Trivia, Cards Against Humanity and more. 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.
Aug 14 (Thurs) Tarrytown Summer Concerts 7-9pm at Pierson Park
The Window
The Tarrytown Summer Concert Series is a lively community tradition that brings music, dancing, and fun to the heart of the village! Set against the scenic backdrop of the Hudson River, families and friends gather each week to enjoy live performances from local bands, food vendors, and a festive, laid-back atmosphere that captures the joy of summer. (June 26-August 28 from 7pm to 9pm)
(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.
(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. Choose from Chess, Checkers, Connect 4, Guess Who, Trivia, Cards Against Humanity and more. 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.
(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. Choose from Chess, Checkers, Connect 4, Guess Who, Trivia, Cards Against Humanity and more. 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.
Aug 28 (Thurs) Tarrytown Summer Concerts 7-9pm at Pierson Park
Billy & The Showmen
The Tarrytown Summer Concert Series is a lively community tradition that brings music, dancing, and fun to the heart of the village! Set against the scenic backdrop of the Hudson River, families and friends gather each week to enjoy live performances from local bands, food vendors, and a festive, laid-back atmosphere that captures the joy of summer. (June 26-August 28 from 7pm to 9pm)
(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.
September
(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. Choose from Chess, Checkers, Connect 4, Guess Who, Trivia, Cards Against Humanity and more. 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.
(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. Choose from Chess, Checkers, Connect 4, Guess Who, Trivia, Cards Against Humanity and more. 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.