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  • The Original Knickerbocker Tour

    The Original Knickerbocker Tour
    Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United States

    The Original Knickerbocker: Washington Irving & “The Legend of Sleepy Hollow”. Meet the father of the American short story on this one-hour tour of Sleepy Hollow Cemetery! Learn all about …

    $15
  • The Original Knickerbocker Tour

    The Original Knickerbocker Tour
    Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United States

    The Original Knickerbocker: Washington Irving & “The Legend of Sleepy Hollow”. Meet the father of the American short story on this one-hour tour of Sleepy Hollow Cemetery! Learn all about …

    $15
  • Tarrytown Dogs on Parade

    Patriots Park Patriots Park, Tarrytown, NY, United States

    The Village of Tarrytown together with the Tarrytown/ Sleepy Hollow Chamber of Commerce and Bark and Meow invite you to join Tarrytown Dogs on Parade. With the 146th Annual Westminster Kennel …

    Free
  • Nick Lowe’s Quality Rock & Roll Review Starring Los Straitjackets

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

    Nick Lowe has made his mark as a producer (Elvis Costello-Graham Parker-Pretenders-The Damned), songwriter of at least three songs you know by heart, short-lived career as a pop star, and …

    $39 – $59
  • Monty Alexander Trio

    Jazz Forum Club Performances
    Jazz Forum Club 1 Dixon Lane, Tarrytown, NY, United States

    Don't miss the legendary jazz pianist Monty Alexander perform at Tarrytown's Jazz Forum! Fifty-five years after he moved to the United States from Kingston, Jamaica, his home town, Monty Alexander …

    $30 – $35
  • Irvington Farmers Market

    Irvington Farmers Market
    Main Street School 101 Main Street, Irvington, NY, United States

    Enjoy live music, river views and a laid-back setting at this small-town Sunday market showcasing the best of what the Hudson Valley has to offer. In season, there is fresh …

    Free
  • Sunnyside Tours

    Sunnyside Tours
    Sunnyside 3 W Sunnyside Lane, Irvington, NY, United States

    A charming, romantic Hudson River landscape. America’s “Founding Father of Literature” created a romantic, picturesque estate nestled along the Hudson riverbank. The enchanted landscape of Washington Irving’s much-loved Sunnyside has …

    $12 – $17
  • Octagon House Classic Tour

    Octagon House Classic Tour
    Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY, United States

    The Armour-Stiner Octagon House, a registered National Historic Landmark, was created as a summer retreat by tea-importer Joseph Stiner. Its shape was based on the theories of Orson Squire Fowler, …

    $29
  • Kykuit Tours

    Kykuit Tours
    Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United States

    Built between 1906 and 1913, Kykuit was home to four generations of the Rockefeller family. In 2022 the site will be open for guided tours Saturday-Sunday from May 21-October 2; …

    $18 – $60
  • Philipsburg Manor Tours

    Philipsburg Manor Tours
    Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United States

    Journey to Colonial America! Wander along a woodland path and enter the year 1750, when Philipsburg Manor was a thriving milling and trading complex that was home to several hundred tenant …

    $12 – $17
  • Old Croton Aqueduct Weir Tour

    Old Croton Aqueduct Weir Tour
    Joseph G. Caputo Community Center 95 Broadway, Ossining, NY, United States

    The Old Croton Aqueduct, New York City's original water supply, runs from, Croton-on-Hudson into the Bronx and Manhattan, passing through Sleepy Hollow and Tarrytown. For most of its length, the Aqueduct …

    Free
  • The Original Knickerbocker Tour

    The Original Knickerbocker Tour
    Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United States

    The Original Knickerbocker: Washington Irving & “The Legend of Sleepy Hollow”. Meet the father of the American short story on this one-hour tour of Sleepy Hollow Cemetery! Learn all about …

    $15
  • Union Church Tours

    Union Church Tours
    Union Church of Pocantico Hills 555 Bedford Road, Sleepy Hollow, NY, United States

    The Union Church of Pocantico Hills is a repository of awe-inspiring art by Matisse & Chagall. Stained-glass windows by European masters, commissioned by the Rockefeller family, adorn this unassuming country …

    $9
  • The Original Knickerbocker Tour

    The Original Knickerbocker Tour
    Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United States

    The Original Knickerbocker: Washington Irving & “The Legend of Sleepy Hollow”. Meet the father of the American short story on this one-hour tour of Sleepy Hollow Cemetery! Learn all about …

    $15
  • The Musical Box Performs Genesis: The Lamb Lies Down on Broadway

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

    The greatest rock opera ever created, The Lamb lies Down on Broadway, the last collaborative effort between legendary Peter Gabriel and Genesis, is to be revived one last time... The …

    $38 – $65
  • Westminster Kennel Club: Masters Obedience Championship and Breed Judging

    Lyndhurst 635 South Broadway, Tarrytown, NY, United States

    Masters Obedience Championship: 8:00am – 4:30pm Obedience is a command-driven competition that tests a dog’s ability to comply with the asks of the handler. Commands can include a combination of …

    $12.5 – $25
  • Octagon House Classic Tour

    Octagon House Classic Tour
    Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY, United States

    The Armour-Stiner Octagon House, a registered National Historic Landmark, was created as a summer retreat by tea-importer Joseph Stiner. Its shape was based on the theories of Orson Squire Fowler, …

    $29
  • Westminster Kennel Club: Breed Judging and Group Judging

    Lyndhurst 635 South Broadway, Tarrytown, NY, United States

    Breed judging Judging of Toy, Terrier, and Non-Sporting breeds and Junior Showmanship Preliminaries 8:00am – 4:30pm Junior Showmanship is a competition assessing the handling skills of children 9-18 years of age-independent …

    $12.5 – $25
  • Kristina Marinova – 4 Rhapsodies

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

    Critically acclaimed pianist Kristina Marinova performs four rhapsodies not often heard together in a live performance. These works for solo piano present a range of technical demands as well as …

    $28 – $48
  • Westminster Kennel Club: Best in Show

    Lyndhurst 635 South Broadway, Tarrytown, NY, United States

    Breed Judging Judging of Sporting and Working breeds and Junior Showmanship Preliminaries 8:00am – 4:30pm Junior Showmanship Finals 7:00pm-7:30pm Group Judging Judging of Sporting, Working, and Terrier Groups ​​​​​​​7:30pm – …

    $12.5 – $25

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.