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  • An Evening with The Yale Whiffenpoofs

    The Ark at the Shames JCC 371 South Broadway, Tarrytown, NY, United States

    Hear the world’s oldest and best-known collegiate a cappella group live at The Ark! Every year, 14 of Yale’s top singers are selected to be in the Whiffenpoofs, the world’s oldest and best-known collegiate a cappella group. Singing a mixture of old Yale tunes, jazz standards, and other hits from across the decades, the Whiffenpoofs …

    $35 – $40
  • Lisa Loeb Live

    The Ark at the Shames JCC 371 South Broadway, Tarrytown, NY, United States

    Experience Lisa Loeb up close in an intimate acoustic performance and conversation about the stories behind her iconic songs. Don’t miss a rare chance to experience singer-songwriter Lisa Loeb up close and unplugged. We’ll transform The Ark into an intimate listening room for a special acoustic set filled with the heartfelt storytelling and iconic melodies …

    $40 – $60
  • Open Mic Night

    Open Mic Night
    Hudson Valley Writers Center 300 Riverside Drive, Sleepy Hollow, NY, United States

    Physical and virtual doors open at 7:20 pm for event starting at 7:30 pm. Due to popular demand to participate, we’ve had to limit the amount of readers to 20. All performers, whether “in person” or on Zoom, will be given a 5 minute spot. The “in person” performers at HVWC will perform. The online, …

    Free – $5
  • Christ Church Spring Fling

    Christ Church San Marcos 43 South Broadway, Tarrytown, NY, United States

    Celebrate the arrival of spring with live jazz, refreshments, a silent auction, raffles, and fun! All proceeds benefit Christ Church San Marcos outreach in the local community and around the world. Washington Irving, author of “The Legend of Sleepy Hollow,” followed the Rev. Dr. William Creighton to this church from Zion Episcopal in Dobbs Ferry. …

    Free
  • Cardboard Explosion: A Paper Heart Puppet Show & Workshop

    The Ark at the Shames JCC 371 South Broadway, Tarrytown, NY, United States

    Spend a springy Sunday morning building your own puppet, taking in a creative puppet show, or both! Enjoy stories brought to life using nothing but recycled cardboard and the power of your imagination! Puppeteer Brad Shur transforms simple cardboard shapes into elaborate puppet characters and tells stories that are sure to wow children of all …

    $20 – $35
  • The People’s Mic with Phylisha Villanueva

    Open Mic Night
    Hudson Valley Writers Center 300 Riverside Drive, Sleepy Hollow, NY, United States

    The People’s Mic is more than an open mic; it’s a community gathering rooted in care, creativity, and connection, hosted by Westchester Poet Laureate Phylisha Villanueva. Join us for an evening where poets, storytellers, and musicians share space and truth. Doors open at 6:30!

    $5
  • Stefan Jackiw, violin and Kevin Ahfat, piano

    Friends Of Music Concerts
    Kusel Auditorium at Sleepy Hollow High School 210 North Broadway, Sleepy Hollow, NY, United States

    One of America’s foremost violinists, Jackiw (pronounced jak-eef’) captivates audiences with playing that combines poetry and purity with an impeccable technique. He recently performed Samuel Barber’s Violin Concerto with the New York Philharmonic. The Boston Globe hailed his “uncommon musical substance” that is “striking for its intelligence and sensitivity.” In 2024, Jackiw performed Tchaikovsky’s violin …

    $40
  • Spring Crafts at Lyndhurst

    Spring Crafts at Lyndhurst
    Lyndhurst 635 South Broadway, Tarrytown, NY, United States

    The Spring Craft Show by ArtRider at Lyndhurst returns from May 1 through May 3 with 200 craftspeople and makers! Shop for one-of-a-kind gifts for Mother’s Day, Father’s Day, graduations, weddings, or just for yourself! Visitors can spend the day with family and friends shopping for original fashions, accessories, jewelry, home décor, furniture, photography, and …

    $6 – $16
  • The Complete Works of William Shakespeare (Abridged)

    Hudson Valley Writers Center 300 Riverside Drive, Sleepy Hollow, NY, United States

    37 Plays. 90 minutes. What could possibly go wrong?! Bring the kids! This one is fun for the whole family! This May, Lovely Calamity Productions invites audiences to stop staring into the void and start pointing at it and laughing. The company kicks off its spring season with the riotously funny and relentlessly entertaining The …

    $30
  • Craig Ferguson – Pants on Fire

    Tarrytown Music Hall Performances
    Tarrytown Music Hall 13 Main Street, Tarrytown, NY, United States

    Craig Ferguson is a multiple Grammy nominated, Peabody and Emmy Award-winning actor, writer, producer, director and comedian with a diverse career that encompasses film, television and the stage. He is a New York Times bestselling author and has recorded numerous standup specials for Netflix, Epix, Comedy Central and Amazon. The wildly popular Late Late Show …

    $47.50 – $67.50
  • Spring Crafts at Lyndhurst

    Spring Crafts at Lyndhurst
    Lyndhurst 635 South Broadway, Tarrytown, NY, United States

    The Spring Craft Show by ArtRider at Lyndhurst returns from May 1 through May 3 with 200 craftspeople and makers! Shop for one-of-a-kind gifts for Mother’s Day, Father’s Day, graduations, weddings, or just for yourself! Visitors can spend the day with family and friends shopping for original fashions, accessories, jewelry, home décor, furniture, photography, and …

    $6 – $16
  • The Complete Works of William Shakespeare (Abridged)

    Hudson Valley Writers Center 300 Riverside Drive, Sleepy Hollow, NY, United States

    37 Plays. 90 minutes. What could possibly go wrong?! Bring the kids! This one is fun for the whole family! This May, Lovely Calamity Productions invites audiences to stop staring into the void and start pointing at it and laughing. The company kicks off its spring season with the riotously funny and relentlessly entertaining The …

    $30
  • Sleepy Hollow Cemetery Lantern Tour

    Sleepy Hollow Cemetery Lantern Tour
    Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United States

    Step back in time and explore the cemetery by kerosene lantern light! This two-hour evening tour gives you a great overview of why Sleepy Hollow Cemetery is so famous. You’ll visit titans of industry like Andrew Carnegie and William Rockefeller, meet Washington Irving whose famous short story gave our village its very name, see the …

    $45
  • Spring Crafts at Lyndhurst

    Spring Crafts at Lyndhurst
    Lyndhurst 635 South Broadway, Tarrytown, NY, United States

    The Spring Craft Show by ArtRider at Lyndhurst returns from May 1 through May 3 with 200 craftspeople and makers! Shop for one-of-a-kind gifts for Mother’s Day, Father’s Day, graduations, weddings, or just for yourself! Visitors can spend the day with family and friends shopping for original fashions, accessories, jewelry, home décor, furniture, photography, and …

    $6 – $16
  • Westchester Ballet Company presents Fairytale Classics—Peter and the Wolf & Cinderella

    Tarrytown Music Hall Performances
    Tarrytown Music Hall 13 Main Street, Tarrytown, NY, United States

    Step into a world of magic and imagination! Westchester Ballet Company presents Fairytale Classics—Peter and the Wolf & Cinderella, a charming one-hour ballet newly choreographed by resident choreographer Sabrina Gail Lobner. This vibrant new production reimagines two timeless favorites, performed by professional guest artists and an exceptional ensemble of young dancers from across the New …

    $28 – $38
  • Brett Goldstein: Sex, Death & Small Talk

    Tarrytown Music Hall Performances
    Tarrytown Music Hall 13 Main Street, Tarrytown, NY, United States

    Brett Goldstein—a breakthrough British creative force on and offscreen — has emerged as one of Hollywood’s most sought-after multihyphenates. He is the co-executive producer, writer, and star of the Peabody-winning Apple TV+ series, “Ted Lasso.” Hailed by fans and critics alike, season three made waves after surpassing its previous record-breaking haul, once again leading as …

    $77 – $158
  • Film Series: Star Wars Episode IV: A New Hope

    Tarrytown Music Hall Performances
    Tarrytown Music Hall 13 Main Street, Tarrytown, NY, United States

    May the Fourth be with You!! Classic films in a classic venue. A farmboy joins forces with various allies to save their galaxy from the evil Empire's planet-destroying battle station, while also rescuing the princess leading the rebellion against them. Runtime: 121 Minutes Directed by George Lucas Starring Mark Hamill, Harrison Ford, Carrie Fisher Rated …

    Free – $11
  • Draft n’ Drink

    Draft n’ Drink
    Hudson Valley Writers Center 300 Riverside Drive, Sleepy Hollow, NY, United States

    Join The Hudson Valley Writers Center (HVWC) and Hudson Valley Books for Humanity (HVBH) for Draft n' Drink! Meet us for an evening of writing prompts and exercises, a beverage, and a fun and casual environment where we can write creatively in community. Participation in the guided writing exercises is voluntary, and participants can share …

    $20
  • The Moth – True Stories Told Live

    Tarrytown Music Hall Performances
    Tarrytown Music Hall 13 Main Street, Tarrytown, NY, United States

    This Spring, globally beloved storytelling institution, The Moth, is bringing back the Mainstage show to Tarrytown. For ONE night, 5 seasoned storytellers will share extraordinary, true stories that dig deep into the idea of the American Dream. Does it even exist anymore? FOR WHO? What happens when the dream rubs up against reality? What happens …

    $47.50 – $73.50
  • Spring Market at Makers Central

    Spring Market at Makers Central
    Makers Central 84 Central Avenue, Tarrytown, NY, United States

    Ceramic lighting, custom woodworks, handmade plateware, concrete goods, handmade paper, organic bird seed, leather and textiles, handmade jewelry, wellness products, baked goods, art, and more! Plus local beer and whiskey tastings.

    Free
  • Taconic Opera presents Kessa Mefford in “Concertos in D”

    Tarrytown Music Hall Performances
    Tarrytown Music Hall 13 Main Street, Tarrytown, NY, United States

    This concert marks the culmination of an eight-year project by Kessa Mefford to publicly perform everything that Ravel ever composed for the piano. She returns to the Tarrytown stage performing Ravel’s famous Concerto in D Major for left-hand along with the world premiere of Dan Montez’s Piano Concerto No. 2 in D minor. Montez’s concerto …

    $28 – $48
  • Murder and Mayhem Walking Tour

    Murder and Mayhem Walking Tour
    Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United States

    The true stories on this two-hour lantern tour of Sleepy Hollow Cemetery are so grim, you just might have nightmares! Curious to learn about a family that lost 5 children one terrible afternoon, or a horrific murder that led police on a multi-state chase? Maybe you’d like to hear about a son who shot his …

    $50
  • Sleepy Hollow Cemetery Lantern Tour

    Sleepy Hollow Cemetery Lantern Tour
    Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United States

    Step back in time and explore the cemetery by kerosene lantern light! This two-hour evening tour gives you a great overview of why Sleepy Hollow Cemetery is so famous. You’ll visit titans of industry like Andrew Carnegie and William Rockefeller, meet Washington Irving whose famous short story gave our village its very name, see the …

    $45
  • Spring Market at Makers Central

    Spring Market at Makers Central
    Makers Central 84 Central Avenue, Tarrytown, NY, United States

    Ceramic lighting, custom woodworks, handmade plateware, concrete goods, handmade paper, organic bird seed, leather and textiles, handmade jewelry, wellness products, baked goods, art, and more! Plus local beer and whiskey tastings.

    Free
  • Open Mic Night

    Open Mic Night
    Hudson Valley Writers Center 300 Riverside Drive, Sleepy Hollow, NY, United States

    Physical and virtual doors open at 7:20 pm for event starting at 7:30 pm. Due to popular demand to participate, we’ve had to limit the amount of readers to 20. All performers, whether “in person” or on Zoom, will be given a 5 minute spot. The “in person” performers at HVWC will perform. The online, …

    Free – $5

There's something for everyone in Sleepy Hollow Country—farmers markets, live music, street fairs, historic homes, hiking trails, kayaking and boating on the Hudson River. Halloween season brings even more for the whole family—haunted hayrides, blazing pumpkins, costumed 10K run, Halloween parade, and of course, the Headless Horseman! For the latest on Fall events, visit our guide to Halloween in Sleepy Hollow.