Tarrytown / Sleepy Hollow NY - Calendar of Things to Do

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

Apr 24 (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.

Apr 26 (Sat) The Tapp's 2nd Annual Halfway to Halloween Bar & Business Crawl and Scavenger Hunt 12-6pm @ The Tapp in Tarrytown

Dust off your costumes! This Halloween-themed scavenger hunt leads costumed teams through Tarrytown, supporting local businesses. Teams get trick-or-treat bags with clues, visiting spots like The Tapp, The Purple Ostrich, The Cube Inn, Horsefeathers and Tarrytown Music Hall before the final party at The Set Back Inn, featuring a costume contest and dance party.

Apr 26 (Sat) Tarrytown Music Hall 8pm

Lyle Lovett

Texas-based musician fuses elements of country, swing, jazz, folk, gospel and blues.

Apr 27 (Sun) Tarrytown Music Hall 11am

The Paper Bag Players: We Start to Sing!

America’s beloved children’s theater company, THE PAPER BAG PLAYERS, has been creating imaginative worlds from paper and cardboard since 1958. Their joyful 66th season show, WE START TO SING! bursts with zany stories, audience participation, sing-along songs, foot-stomping dances, larger-than-life characters, and art brought to life on a giant easel. It’s a funny, friendly, and thrilling hour of theater – perfect for children ages 3 through 9, perfect for everyone!

Apr 27 (Sun) Tarrytown Duck Derby 11am-3pm

The Tarrytown Rotary Club's Duck Derby will take place on Saturday, April 26, 2025, at Patriots Park, featuring exciting rubber duck races, family-friendly activities, and community fun.

Apr 28 (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!

Apr 29 (Tues) Trivia Night 7pm at The Tapp (A fun local bar)

Free to Play! 1st & 2nd Place teams win gift certificates.

May 1 (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 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)

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)

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)

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)

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)

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.

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The Headless Horseman's Calendar