The Headless Horseman's Calendar
Tarrytown & Sleepy Hollow, NY
Also check out our list of entertaining things to do happening all the time
(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-Sep 11 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.
August 8 (Fri) Tarrytown Music Hall 7pm
Once Upon a One More Time
Based on a Broadway musical that uses the music of Britney Spears to tell a feminist-inspired story about classic fairytale characters rewriting their "happily ever afters". The show, which premiered in 2023, features iconic characters like Cinderella, Snow White, and the Little Mermaid, who are re-imagined as part of a book club.
Presented by The Music Hall Academy. Performed by high school and college performers.
Director: Jordan Singer. Choreographer: Deb Toteda.
August 8 (Fri) Tarrytown Friday Night Concert Series 6:30-8pm at Pierson Park
The unparalleled views of the bridge and the Hudson River create a joyful ambience for picnics with family and friends, while experiencing the finest emerging and established Jazz artists and groups.
August 9 (Sat) Tarrytown Music Hall 7pm
Once Upon a One More Time
Based on a Broadway musical that uses the music of Britney Spears to tell a feminist-inspired story about classic fairytale characters rewriting their "happily ever afters". The show, which premiered in 2023, features iconic characters like Cinderella, Snow White, and the Little Mermaid, who are re-imagined as part of a book club.
Presented by The Music Hall Academy. Performed by high school and college performers.
Director: Jordan Singer. Choreographer: Deb Toteda.
(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-Sep 11 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.
August 15 (Fri) Tarrytown Friday Night Concert Series 6:30-8pm at Pierson Park
The unparalleled views of the bridge and the Hudson River create a joyful ambience for picnics with family and friends, while experiencing the finest emerging and established Jazz artists and groups.
(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.
August 22 (Fri) Tarrytown Friday Night Concert Series 6:30-8pm at Pierson Park
The unparalleled views of the bridge and the Hudson River create a joyful ambience for picnics with family and friends, while experiencing the finest emerging and established Jazz artists and groups.
(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-Sep 11 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.
August 29 (Fri) Tarrytown Friday Night Concert Series 6:30-8pm at Pierson Park
The unparalleled views of the bridge and the Hudson River create a joyful ambience for picnics with family and friends, while experiencing the finest emerging and established Jazz artists and groups.
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.
Sep 4 (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-Sep 11 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.
Sept 11 (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-Sep 11 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.
October