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 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 11am - 3pm
Celebrate Mother's Day in Tarrytown with the Open Streets event. Main Street will be closed to cars and open to shopping, dining and strolling with friends and neighbors. Come celebrate mom and enjoy live music with Kendra Valentine and Clare Maloney, a fashion show, face painting and more!
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 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.