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 3 (Sat) Rock the Riverbank pm at Horan’s Landing
A lively community event at Horan’s Landing, featuring live music, local vendors, family-friendly activities, and beautiful riverside views. Don’t miss out on the fun!
May 3 (Sat) Tarrytown Music Hall 8pm
Yacht Rock Gold Experience
Yacht Rock Gold Experience brings all your favorite hits from the late 1970's-early 1980's to new generations of music fans. Celebrating the smooth sounds of the Doobie Brothers, Fleetwood Mac, Steely Dan, Christopher Cross, Kenny Loggins, Little River Band, Ambrosia, Boz Skaggs and so many more, Yacht Rock Gold engages fans with amazing harmonies and musicianship that brings audiences back to a time when music made you feel good and soothed the soul.
May 4 (Sun) Friends of Music 3pm at Sleepy Hollow High School Auditorium
Jerusalem String Quartet
We are proud to bookend our 24-25 season with brilliant artists who uphold the glorious traditions of the string quartet – Han, Setzer, Finckel, who opened, and the members of the Jerusalem String Quartet, who will conclude the season.
May 4 (Sun) Tarrytown Music Hall 7pm
Al Stewart & Livingston Taylor
Al Stewart rose to fame during the British folk revival of the 60s and 70s, blending folk-rock with historical tales. Known for his hits "Year of the Cat" and "Time Passages," Stewart's career spans four decades, including performing at the first Glastonbury Festival in 1970. Taylor's songs have been recorded by his brother James, and he has performed with Joni Mitchell, Linda Ronstadt, Fleetwood Mac, and Jimmy Buffet.
May 5 (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 6 (Tues) Trivia Night 7pm at The Tapp (A fun local bar)
Free to Play! 1st & 2nd Place teams win gift certificates.
May 8 (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 11 (Sun) Tarrytown Open Streets Time tba
Celebrate Mother's Day in Tarrytown with the Open Streets event.
May 12 (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 13 (Tues) Trivia Night 7pm at The Tapp (A fun local bar)
Free to Play! 1st & 2nd Place teams win gift certificates.
May 15 (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 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 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.
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 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 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 Time tba
Celebrate Gay Pride in Tarrytown with the Open Streets event.
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 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) 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.