Sleepy Hollow Halloween 2024 Dates. Celebrate the 200th anniversary of the legend of sleepy hollow at conner prairie's beloved headless horseman festival. If the first weekend of october falls during your trip, be sure to swing by the sleepy hollow street fair where you can discover food, music, local shops, arts & crafts,.

Sleepy hollow ‘run for your life’ halloween 10k. Planning the ultimate halloween trip to sleepy hollow, ny;