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
May 17 (Sat) Tarrytown Music Hall 8pm
Leonid & Friends - Celebrating the Music of Chicago
LEONID & FRIENDS have blown the minds of legions of fans with their uncanny ability to capture the spirit, musicality, and fire of American supergroup Chicago. Leonid Vorobyev's goal was a studio project in dedication to Chicago under the motto “musicians for musicians”. Their first video went viral, but they really gained traction when Chicago itself published the video on its official website. They have since expanded their repertoire to include Earth Wind & Fire, Blood Sweat & Tears, Ides of March, Stevie Wonder, Steely Dan, Deep Purple, and new original material.
May 19 (Mon) Game Night 5pm-Mid at The Tapp (A fun local bar)
Come watch Monday Night Football with us or grab one of our board games and have some fun. Choose from Chess, Checkers, Connect 4, Candyland, Guess Who, Trivia, Cards Against Humanity and more. Have a different one in mind? Bring your own!
May 20 (Tues) Trivia Night 7pm at The Tapp (A fun local bar)
Free to Play! 1st & 2nd Place teams win gift certificates.
May 22 (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.
May 23 (Fri) Tarrytown Music Hall 8pm
The Machine Performs Pink Floyd
May 24 (Sat) Pinkster Festival tba at Philipsburg Manor
Celebrate African American history and culture with music, dance, storytelling, and traditional crafts honoring the legacy of Pinkster.
May 26 (Mon) Game Night 5pm-Mid at The Tapp (A fun local bar)
Come watch Monday Night Football with us or grab one of our board games and have some fun. Choose from Chess, Checkers, Connect 4, Candyland, Guess Who, Trivia, Cards Against Humanity and more. Have a different one in mind? Bring your own!
May 27 (Tues) Trivia Night 7pm at The Tapp (A fun local bar)
Free to Play! 1st & 2nd Place teams win gift certificates.
May 29 (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.
May 30 (Fri) Tarrytown Music Hall 8pm
Dead On Live - Grateful Dead 71’-72’
Dead On Live’s return to Tarrytown will feature the music from the beloved “live” era releases of 1971-1972, featuring favorites from “Skull and Roses”, Jerry’s 1st solo effort “Garcia”, the classic and revered “Europe 72” and more from Bob Weir’s 1st solo effort “Ace”. Songs such as “Wharf Rat”, “The Wheel”, “China Cat Sunflower/I Know You Rider” (In it’s entirety!), “Mexicali Blues” and “One More Saturday Night” will be performed as they were recorded, all instruments and vocals.
May 31 (Sat) Tarrytown Music Hall 8pm
Brian Regan
Critics, fans and fellow comedians agree: Brian Regan is one of the most respected comedians in the country with Vanity Fair calling Brian, “The funniest stand-up alive,” and Entertainment Weekly calling him, “Your favorite comedian’s favorite comedian.” Having built his 30-plus year career on the strength of his material alone, Brian’s non-stop theater tour continuously fills the most beautiful venues across North America, visiting close to 100 cities each year.
June 1 (Sun) Tarrytown Street Fair 10am on Main St
Don't miss out on the Tarrytown Street Fair – an unforgettable annual event that takes over Main Street in Tarrytown, New York! With over 100 vendors offering everything from unique crafts to delicious food and local treasures, there’s something for everyone. Enjoy live entertainment throughout the day, making it the perfect outing for friends, families, and visitors alike. Whether you're a local or just passing through, the Tarrytown Street Fair is the place to be!
June 2 (Mon) Game Night 5pm-Mid at The Tapp (A fun local bar)
Come watch Monday Night Football with us or grab one of our board games and have some fun. Choose from Chess, Checkers, Connect 4, Candyland, 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 Football with us or grab one of our board games and have some fun. Choose from Chess, Checkers, Connect 4, Candyland, 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 Football with us or grab one of our board games and have some fun. Choose from Chess, Checkers, Connect 4, Candyland, 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 Football with us or grab one of our board games and have some fun. Choose from Chess, Checkers, Connect 4, Candyland, 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 Football with us or grab one of our board games and have some fun. Choose from Chess, Checkers, Connect 4, Candyland, Guess Who, Trivia, Cards Against Humanity and more. Have a different one in mind? Bring your own!
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 Football with us or grab one of our board games and have some fun. Choose from Chess, Checkers, Connect 4, Candyland, 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) 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.