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  • Aquefest!

    Aqueduct Keepers House 15 Walnut Street, Dobbs Ferry, NY

    Get ready for Aquefest! Come to the Keeper’s House to celebrate the Aqueduct and life on the trail with Goat On A Boat Puppets, a petting farm, the Rivertown Ramblers, …

    Free
  • This is a view of the 2022 Great Jack O'Lantern Blaze at Van Cortlandt Manor in Corton-on-Hudson, N.Y. on September 14, 2022.

    The Great Jack O’Lantern Blaze

    The Great Jack O’Lantern Blaze
    Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson, NY, United States

    Bigger, Brighter, and More Spectacular Than Ever Before! The Great Jack O'Lantern Blaze is the Hudson Valley’s most electrifying fall happening! Meander through the 18th-century landscape of Van Cortlandt Manor …

    $24 – $50
  • Fresh yellow and green squash at Tarrytown and Sleepy Hollow Farmers Market.

    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
  • Sleepy Hollow Street Fair tent by J & G Deli features baked goods.

    Sleepy Hollow Street Fair

    Beekman Avenue, Sleepy Hollow Beekman Avenue, Sleepy Hollow, NY, United States

    Discover the magic of autumn at the Sleepy Hollow Street Fair, presented by the Sleepy Hollow Tarrytown Chamber of Commerce! On Sunday, September 21, immerse yourself in a bustling community …

    Free
  • This is a view of the 2022 Great Jack O'Lantern Blaze at Van Cortlandt Manor in Corton-on-Hudson, N.Y. on September 14, 2022.

    The Great Jack O’Lantern Blaze

    The Great Jack O’Lantern Blaze
    Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson, NY, United States

    Bigger, Brighter, and More Spectacular Than Ever Before! The Great Jack O'Lantern Blaze is the Hudson Valley’s most electrifying fall happening! Meander through the 18th-century landscape of Van Cortlandt Manor …

    $24 – $50
  • This is a view of the 2022 Great Jack O'Lantern Blaze at Van Cortlandt Manor in Corton-on-Hudson, N.Y. on September 14, 2022.

    The Great Jack O’Lantern Blaze

    The Great Jack O’Lantern Blaze
    Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson, NY, United States

    Bigger, Brighter, and More Spectacular Than Ever Before! The Great Jack O'Lantern Blaze is the Hudson Valley’s most electrifying fall happening! Meander through the 18th-century landscape of Van Cortlandt Manor …

    $24 – $50
  • This is a view of the 2022 Great Jack O'Lantern Blaze at Van Cortlandt Manor in Corton-on-Hudson, N.Y. on September 14, 2022.

    The Great Jack O’Lantern Blaze

    The Great Jack O’Lantern Blaze
    Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson, NY, United States

    Bigger, Brighter, and More Spectacular Than Ever Before! The Great Jack O'Lantern Blaze is the Hudson Valley’s most electrifying fall happening! Meander through the 18th-century landscape of Van Cortlandt Manor …

    $24 – $50
  • This is a view of the 2022 Great Jack O'Lantern Blaze at Van Cortlandt Manor in Corton-on-Hudson, N.Y. on September 14, 2022.

    The Great Jack O’Lantern Blaze

    The Great Jack O’Lantern Blaze
    Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson, NY, United States

    Bigger, Brighter, and More Spectacular Than Ever Before! The Great Jack O'Lantern Blaze is the Hudson Valley’s most electrifying fall happening! Meander through the 18th-century landscape of Van Cortlandt Manor …

    $24 – $50
  • Fresh produce from Berry Brook Farm at Tarrytown and Sleepy Hollow Farmers Market.

    TaSH Farmers Market

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

    Stop by TaSH, Tarrytown’s and Sleepy Hollow’s weekly farmers market, for fresh Hudson Valley produce, meat, bread, cut flowers, dairy products, preserves, wine, and beer. There are weekly live music performances, …

    Free
  • Kathryn W. Davis RiverWalk Center in Sleepy Hollow is decorated with sheaves of corn, pumpkins and chrysanthemums ahead of Oktoberfest celebration.

    Sleepy Hollow Oktoberfest

    Kingsland Point Park 299 Palmer Avenue, Sleepy Hollow, NY, United States

    Sleepy Hollow's 13th Annual Oktoberfest in Kingsland Point Park! Feast on German food and beer from local eateries and dance to live Bavarian music at Sleepy Hollow's annual Oktoberfest! Cider …

    Free
  • This is a view of the 2022 Great Jack O'Lantern Blaze at Van Cortlandt Manor in Corton-on-Hudson, N.Y. on September 14, 2022.

    The Great Jack O’Lantern Blaze

    The Great Jack O’Lantern Blaze
    Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson, NY, United States

    Bigger, Brighter, and More Spectacular Than Ever Before! The Great Jack O'Lantern Blaze is the Hudson Valley’s most electrifying fall happening! Meander through the 18th-century landscape of Van Cortlandt Manor …

    $24 – $50
  • Fresh yellow and green squash at Tarrytown and Sleepy Hollow Farmers Market.

    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
  • This is a view of the 2022 Great Jack O'Lantern Blaze at Van Cortlandt Manor in Corton-on-Hudson, N.Y. on September 14, 2022.

    The Great Jack O’Lantern Blaze

    The Great Jack O’Lantern Blaze
    Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson, NY, United States

    Bigger, Brighter, and More Spectacular Than Ever Before! The Great Jack O'Lantern Blaze is the Hudson Valley’s most electrifying fall happening! Meander through the 18th-century landscape of Van Cortlandt Manor …

    $24 – $50
  • This is a view of the 2022 Great Jack O'Lantern Blaze at Van Cortlandt Manor in Corton-on-Hudson, N.Y. on September 14, 2022.

    The Great Jack O’Lantern Blaze

    The Great Jack O’Lantern Blaze
    Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson, NY, United States

    Bigger, Brighter, and More Spectacular Than Ever Before! The Great Jack O'Lantern Blaze is the Hudson Valley’s most electrifying fall happening! Meander through the 18th-century landscape of Van Cortlandt Manor …

    $24 – $50
  • This is a view of the 2022 Great Jack O'Lantern Blaze at Van Cortlandt Manor in Corton-on-Hudson, N.Y. on September 14, 2022.

    The Great Jack O’Lantern Blaze

    The Great Jack O’Lantern Blaze
    Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson, NY, United States

    Bigger, Brighter, and More Spectacular Than Ever Before! The Great Jack O'Lantern Blaze is the Hudson Valley’s most electrifying fall happening! Meander through the 18th-century landscape of Van Cortlandt Manor …

    $24 – $50

  • This is a view of the 2022 Great Jack O'Lantern Blaze at Van Cortlandt Manor in Corton-on-Hudson, N.Y. on September 14, 2022.

    The Great Jack O’Lantern Blaze

    The Great Jack O’Lantern Blaze
    Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson, NY, United States

    Bigger, Brighter, and More Spectacular Than Ever Before! The Great Jack O'Lantern Blaze is the Hudson Valley’s most electrifying fall happening! Meander through the 18th-century landscape of Van Cortlandt Manor …

    $24 – $50

  • Spooky Board Games

    Spooky Board Games
    New Kawaii 1 Bridge Street, Suite 105, Irvington, NY, United States

    Game Night at New Kawaii Join us on Wednesdays at 7PM for Game Night for Grown Ups and Young Adults (teens are welcome!) All October: Dare to Roll! The midweek …

    $5
  • This is a view of the 2022 Great Jack O'Lantern Blaze at Van Cortlandt Manor in Corton-on-Hudson, N.Y. on September 14, 2022.

    The Great Jack O’Lantern Blaze

    The Great Jack O’Lantern Blaze
    Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson, NY, United States

    Bigger, Brighter, and More Spectacular Than Ever Before! The Great Jack O'Lantern Blaze is the Hudson Valley’s most electrifying fall happening! Meander through the 18th-century landscape of Van Cortlandt Manor …

    $24 – $50
  • Headless Horseman Files at Philipsburg Manor.

    The Headless Horseman Files

    The Headless Horseman Files
    Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United States

    Immerse yourself in this Sleepy Hollow whodunit and decide for yourself what really happened to Ichabod Crane. Follow your guide on a mysterious 45-minute walk through the historic grounds of …

    $25 – $30
  • This is a view of the 2022 Great Jack O'Lantern Blaze at Van Cortlandt Manor in Corton-on-Hudson, N.Y. on September 14, 2022.

    The Great Jack O’Lantern Blaze

    The Great Jack O’Lantern Blaze
    Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson, NY, United States

    Bigger, Brighter, and More Spectacular Than Ever Before! The Great Jack O'Lantern Blaze is the Hudson Valley’s most electrifying fall happening! Meander through the 18th-century landscape of Van Cortlandt Manor …

    $24 – $50

  • Spirits of Sleepy Hollow Country

    Spirits of Sleepy Hollow Country
    Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United States

    A Night of Legendary Magic Featuring Mark Clearview & Nick Wallace Join master illusionists as they journey into the realm of the unknown at this spooky supernatural spectacle. Their tricks …

    $65
  • Fresh produce from Berry Brook Farm at Tarrytown and Sleepy Hollow Farmers Market.

    TaSH Farmers Market

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

    Stop by TaSH, Tarrytown’s and Sleepy Hollow’s weekly farmers market, for fresh Hudson Valley produce, meat, bread, cut flowers, dairy products, preserves, wine, and beer. There are weekly live music performances, …

    Free
  • Headless Horseman Files at Philipsburg Manor.

    The Headless Horseman Files

    The Headless Horseman Files
    Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United States

    Immerse yourself in this Sleepy Hollow whodunit and decide for yourself what really happened to Ichabod Crane. Follow your guide on a mysterious 45-minute walk through the historic grounds of …

    $25 – $30
  • This is a view of the 2022 Great Jack O'Lantern Blaze at Van Cortlandt Manor in Corton-on-Hudson, N.Y. on September 14, 2022.

    The Great Jack O’Lantern Blaze

    The Great Jack O’Lantern Blaze
    Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson, NY, United States

    Bigger, Brighter, and More Spectacular Than Ever Before! The Great Jack O'Lantern Blaze is the Hudson Valley’s most electrifying fall happening! Meander through the 18th-century landscape of Van Cortlandt Manor …

    $24 – $50

  • Spirits of Sleepy Hollow Country

    Spirits of Sleepy Hollow Country
    Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United States

    A Night of Legendary Magic Featuring Mark Clearview & Nick Wallace Join master illusionists as they journey into the realm of the unknown at this spooky supernatural spectacle. Their tricks …

    $65

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.