The Headless Horseman's Calendar

Tarrytown & Sleepy Hollow, NY

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

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 Music Hall 7:30pm

Michael Blaustein: The Taste Me Tour

Michael Blaustein is one of the fastest rising stand up comedians working today. His viral stand up comedy clips have amassed over 900 Million views across all social media platforms. He has sold out venues across the world, most recently closing out his successful 2024 tour year with over 72,000 tickets sold.

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.

Sep 5 (Fri) Tarrytown Music Hall 8pm

One Night of Queen performed by Gary Mullen & the Works

For over 20 years Gary Mullen & The Works have been performing their world-renowned One Night of Queen live concert. Gary Mullen & The Works featuring Gary Mullen on vocals, David Brockett on guitar, Malcolm Gentles on keyboards, Jon Halliwell on drums and Alan McGeoch on bass guitar will have you dancing in the aisles during their show, while the band pays tribute to the stage theatrics, showmanship, and music of arguably the greatest rock band of all time: Queen.

Sep 6 (Sat) Tarrytown Music Hall 7pm

Rock The Hall 2025

Rock The Hall is designed to celebrate and elevate emerging and well-deserving musicians from the region. Our judges, and prizes offer artists uplifting opportunities, including performance in front of a live audience, and a first-rate panel of industry professionals. The premise is a good-natured, fun-filled evening of fantastic music, camaraderie, and community-building. Rock The Hall is also a fundraiser to support our local historic landmark theater. Soul Brewery will be here as well to debut and offer tastings of our new exclusive Music Hall Lager!

(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.

Sep 23 (Tues) Tarrytown Music Hall 8 & 9pm

Ghost Tours of The Music Hall

Step into the eerie excitement of the Tarrytown Music Hall's ghost tours, where Master Storyteller Jonathan Kruk brings history and haunting tales to life! Explore the historic lore and discover the spirits lingering in this magnificent 1885 building, once a playground for Millionaires' Colony families like the Rockefellers and Vanderbilts. As you traverse its halls and learn about its storied past – from grand balls to wartime struggles – you'll uncover why some souls may have chosen to never leave. The Tarrytown Music Hall is an official site of the Haunted History Trail of New York State, and paranormal investigators have detected intriguing paranormal activity here. Get ready for a captivating and fun journey into the spooky side of history!

October

(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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