The Headless Horseman's Calendar

Tarrytown & Sleepy Hollow, NY

Also check out our list of entertaining things to do happening all the time

June 28 (Sat) Tarrytown Music Hall 8pm

Al Di Meola - Acoustic Band

Al Di Meola, a living legend in the world of guitar, has been at the forefront of contemporary music for over five decades. His innovative blend of complex rhythmic syncopation, lyrical melodies, and sophisticated harmonies has earned him critical acclaim and widespread recognition, including induction into the Guitar Player Magazine Gallery of Greats. With four gold albums, two platinum albums, and over six million record sales worldwide, Di Meola’s artistry has left an indelible mark on music history.

June 29 (Sun) Tarrytown Music Hall 4:30pm

Priyanka Barve - Live in Concert - Celebrating Legendary Divas

Get Ready for a Musical Night Like No Other!
Join Priyanka Barve on a soulful journey as she pays homage to the legendary female singers who inspired her! This unforgettable concert features Priyanka's own renditions of beloved songs from iconic vocalists like Lata Ji, Asha Ji, Begam Akhtar, and more. Expect a thrilling mix of Bollywood classics, Ghazals, Thumri, Sufi, Semi-Classical, Lavani, Qawwali, and more! With Sunayana Kachroo's captivating narration and Aditya Ranade's soulful vocals, this concert promises to be an emotional and musical experience like no other.

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.

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