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  • A runner on the Ash Tree Loop trail of Rockefeller State Park Preserve practices for Rocky’s 5K.

    Rocky’s 5k

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

    Beautiful fall foliage is the perfect backdrop for Rocky’s 5K. Challenging hills and wide carriage roads – the perfect race for experienced trails runners and first timers. If you are familiar …

    $30 – $50
  • The headless horseman leads the start of Sleepy Hollow Halloween 10k.

    Sleepy Hollow Halloween 10K

    Morse School 30 Pocantico Street, Sleepy Hollow, NY, United States

    The Headless Horseman sends off costumed runners from Beekman Avenue on a 6.2-mile loop through some of the most storied ground in American literature. The certified USATF course winds through …

    $45 – $55

  • Runners crowd a trail in Rockefeller State Park during the Pocantico Hills Marathon.

    Pocantico Hills Marathon & Half Marathon

    Rockwood Hall Phelps Way, Pleasantville, NY, United States +1 more

    Come run the Pocantico Hills Marathon or Half Marathon in Rockefeller State Park Preserve! These single loop courses are rolling and hilly with views of the Hudson River and Palisades. …

    $100 – $225
  • Turdy Dunbar Turkey Trot Poster

    Trudy Dunbar Memorial 5K Turkey Trot & 1 mile Gobbler Trot

    Tarrytown Senior Building 240 W. Main Street, Tarrytown, NY

    Calling all runners & trotters! Tarrytown Recreation is hosting its annual Trudy Dunbar Memorial 5K Turkey Trot & 1 mile Gobbler Trot on Sunday, November 22, 2026 at the Tarrytown …

    $27.50 – $32.80

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.