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 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.

Apr 4 (Fri) Tarrytown Music Hall 8pm

The Magnetic Fields - 69 Love Songs 25th Anniversary Tour

The Magnetic Fields perform their entire 69 Love Songs album in its entirety over the course of 2 nights —a 3-disc masterwork that marked a significant breakthrough for the American band. The band will be performing the full record for the first time in over two decades.

Apr 5 (Sat) Pollinator Garden Flower Seeds Giveaway 12-2pm at The Purple Ostrich

Free Flower Seeds!! See how easy it is to get started with a fool-proof pollinator garden. Tips and tricks, carefree and easy plants, how to source plants, and easy design tips will be offered. Offered in collaboration with Tarrytown Pollinator Pathway, designers of the public pollinator pathway gardens and containers in Tarrytown.

Apr 5 (Sat) Tarrytown Music Hall 8pm

The Magnetic Fields - 69 Love Songs 25th Anniversary Tour

Apr 5 (Sat) 8pm at Tre Angelina restaurant

The Westchester Comedy Club

If you're looking to laugh locally, the founders of "Rye Comedy Club" - a monthly Thursday show that usually sells out, are expanding to a Saturday night laugh-fest in White Plains called "Westchester Comedy Club." The inaugural show will feature five stand-up comedians from New York City.

APR 6 (Sun) Friends of Music 3pm at Sleepy Hollow High School Auditorium

Harmony Zhu, piano

till in her teens, Harmony Zhu, our YCA Performance Award winner, has already had a remarkable career. She won the 2021 Young Concert Artists Susan Wadsworth International Auditions and, at age 10, was named a Young Steinway Artist. In addition, Zhu has appeared as soloist with esteemed orchestras worldwide, including the Philadelphia Orchestra, Chicago Symphony Orchestra and Israel Philharmonic.

Apr 6 (Sun) Tarrytown Music Hall 7pm

HYPROV: Improv under Hypnosis Starring Colin Mochrie & Asad Mecci

Created by improv and comedy legend Colin Mochrie ("Whose Line Is It Anyway?"), and co-star World Renowned Hypnotist Asad Mecci, HYPROV has been called "hilarious and fascinating'' by Time Out New York and "catnip for those who relish spontaneity and informality" by The Wall Street Journal. The New Yorker says, "say yes to HYPROV!"

The 90 minute live show combines hypnosis and improv - two art forms that have mystified and entertained fans, skeptics, and everyone in between worldwide - for a totally unique comedy experience that The Times of London declared "a celebration of the human imagination."

Apr 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!

Apr 8 (Tues) Trivia Night 7pm at The Tapp (A fun local bar)

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

Apr 10 (Thurs) Tarrytown Music Hall 8pm

Black Violin - Full Circle Tour

Step into Black Violin’s Full Circle Tour, where GRAMMY-nominated duo Wil Baptiste and Kev Marcus redefine the possibilities of music by merging classical depth with hip-hop’s pulse. This tour captures the essence of returning to where it all began—transformed and reimagined. Each powerful performance invites audiences to reflect on their own journeys, discovering that even as we evolve, we’re often drawn back to our roots with renewed purpose.

Apr 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.

Apr 11 (Fri) Tarrytown Music Hall 8pm

Lez Zeppelin: Earl's Court '75 The Greatest Led Zeppelin Show Performed in its Entirety

Lez Zeppelin, the all-female band that channels the iconic energy, alchemy and power of Led Zeppelin, will perform the legendary concert: Earl's Court 1975, in its entirety at the Tarrytown Music Hall on April 11, 2025. Hailed by critics as one of Led Zeppelin’s most legendary performances, Earl’s Court is a stunning example of one of the world’s greatest bands at the height of its powers.

Apr 12 (Sat) Sleepy Hollow & Tarrytown Egg Hunt 10am at Patriots Park

The Spring Eggstravaganza at Patriots Park in Tarrytown, NY, is scheduled for Saturday, April 12, 2025, with a rain date of April 19. The event features three egg hunt sessions: 10:00 AM for children aged 3 and under, 10:45 AM for ages 4-5, and 11:30 AM for ages 6-8.

Apr 14 (Mon) Game Night 5pm-Mid at The Tapp (A fun local bar)

Apr 15 (Tues) Trivia Night 7pm at The Tapp (A fun local bar)

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

Apr 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.

Apr 18 (Fri) Tarrytown Music Hall 8pm

Our House - The Music of CSNY

Prepare for an unparalleled musical experience as "OUR HOUSE: The Music of CSNY" assembles to perform the Crosby, Stills, Nash & Young repertoire with an extraordinary ensemble of musical friends. What sets this apart is the stellar, historic lineup.

Apr 21 (Mon) Game Night 5pm-Mid at The Tapp (A fun local bar)

Apr 22 (Tues) Trivia Night 7pm at The Tapp (A fun local bar)

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

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) 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 26 (Sat) 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 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 Cube Inn, Horsefeathers and Tarrytown Music Hall before the final party at The Set Back Inn, featuring a costume contest and dance party.

Apr 27 (Sun) Tarrytown Music Hall 8pm

Lyle Lovett

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

Apr 28 (Mon) Game Night 5pm-Mid at The Tapp (A fun local bar)

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 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 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