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  • 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
  • Nick Kroll: Middle-Aged Boy Tour

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

    Nick Kroll has established himself as one of today’s most sought-after creators, writers, producers, and actors in both film and television.  Dubbed “the Picasso of Puberty” by The New York …

    $35
  • 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
  • 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
  • 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
  • Michel Camilo – Solo Piano!

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

    Pianist Michel Camilo is the winner of too many honors to list – including a Grammy, three Latin Grammys and an Emmy Award. He brings to Jazz Forum his extraordinary solo …

    $40 – $45
  • Max Weinberg’s Jukebox

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

    Performing over 250 shows since April of 2017, Max Weinberg’s Jukebox continues to barnstorm the country, blasting out the hits! As Chuck Berry instructed us in his classic “School Days,”...drop …

    $38 – $55
  • Michel Camilo – Solo Piano!

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

    Pianist Michel Camilo is the winner of too many honors to list – including a Grammy, three Latin Grammys and an Emmy Award. He brings to Jazz Forum his extraordinary solo …

    $40 – $45
  • Michel Camilo – Solo Piano!

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

    Pianist Michel Camilo is the winner of too many honors to list – including a Grammy, three Latin Grammys and an Emmy Award. He brings to Jazz Forum his extraordinary solo …

    $40 – $45
  • TaSH Farmers Market

    Tarrytown and Sleepy Hollow Farmers Market
    Patriots Park Patriots Park, Tarrytown, NY, United States

    Fresh Hudson Valley produce, meat, bread, honey, specialty foods, cut flowers, dairy products, beer and wine. There is live music and sometimes demonstrations of traditional crafts. Route 9 (Broadway) next …

    Free
  • Hike with Mike: “Know Your Limits” Part 2

    Rockefeller State Park Preserve 125 Phelps Way, Pleasantville, NY, United States

    Get to know your pace and preferred distance in this series of three hikes in Rockefeller State Park Preserve, taking place over three months and guided by Mike Miernik. Our …

    $3
  • 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
  • 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
  • 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
  • Ramblin’ Dan’s Freewheelin’ Band

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

    An interactive, multi-genre concert for kids and families. Featuring Ramblin' Dan on guitar along with Sean and Yan on drums and keyboards! Known around NYC as the best children's musician …

    $8
  • 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
  • Roger McGuinn

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

    The Grammy Award singer/songwriter tours the world delighting audiences with the songs and stories from his long and continually productive musical career. Most notably, he was a founding member of …

    $30 – $45
  • Michel Camilo – Solo Piano!

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

    Pianist Michel Camilo is the winner of too many honors to list – including a Grammy, three Latin Grammys and an Emmy Award. He brings to Jazz Forum his extraordinary solo …

    $40 – $45
  • 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

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.