Headless Horseman Chase Route

October 24, 2011 — Washington Irving used actual Sleepy Hollow/Tarrytown, NY, landmarks in his story, The Legend of Sleepy Hollow. On my most recent visit to the area, I retraced and video’d the route of Ichabod Crane from the moment he meets the Headless Horseman to the point where he ends up as a smashed jack-o-lantern and a legend worth the acting talents of Johnny Depp, Jeff Goldblum, and Ed Begley, Jr. More information about all the sites mentioned in Irving’s story can be found here, and other more detailed records of my own jaunts to Sleepy Hollow can be found here and here.

There’s just something about the Headless Horseman that repeatedly draws me to sites connected to him. Maybe I’m just enamored with the idea of life without a head. It sounds pretty stress-free.


  1. Looks like you made an illegal right on red at the high school!

    Did you get to eat at Horsefeathers? They've got the best sweet potato fries.

  2. Oh, the chuchyard is beautiful...as a taphophile, I must add it to my "visit" list. Thanks for the video, so fun!

  3. My daughter goes to college near Sleepy Hollow and took us there in September. It was lots of fun and really lovely -- especially on the trail behind the cemetery. Great video except it made me a little sick to my stomach.