For many, there is nothing more ideal on a chilly and dark October night than to enjoy a scary story. I go out of my way to read as many horror novels as I can during this spookiest of all seasons. But what if there was a book that gave us the history of a figure who preexisted the celebration of Halloween itself? J. W. Ocker has done just that with a terrific work of nonfiction that explores Washington Irving’s most frightening creation.

In his introduction to CHASING THE HEADLESS HORSEMAN, Ocker presents “the galloping Hessian,” as he refers to the dark, perhaps supernatural, figure who purportedly claimed the life --- and head --- of Ichabod Crane in Irving’s “The Legend of Sleepy Hollow.” He also strongly suggests that we read or re-read that classic tale first in order to fully appreciate what he is about to explore for us. We will learn all about the town once known as North Tarrytown, which later was renamed Sleepy Hollow in honor of the story that made the area famous and brings nearly as many tourists during this time of year as Salem, Massachusetts does.

"CHASING THE HEADLESS HORSEMAN shines a light on a tale that has taken on a life of its own --- and in doing so has embedded itself into the culture of our country and the Halloween season forever."

The Headless Horseman can be found everywhere in Sleepy Hollow --- from street signs to fire trucks, and even as the extremely cool name of Sleepy Hollow High School’s official sports mascot. Ocker wanders around the village and takes in the sights and locales that once inspired Irving to pen the most supernatural and gothic horror work he ever produced.

One of the most prominent and creepy parts of Sleepy Hollow is the cemetery where not only the real Hessian who inspired the Headless Horseman is buried but also Irving himself. Irving was born and raised in the UK, but he became so taken with the US that he moved to Sunnyside, a historic house nestled along the banks of the Hudson River.

Ocker talks about taking the same route through the cemetery that the Headless Horseman chased Ichabod Crane down on that fateful night, including the bridge where he ultimately disposed of Crane. A statue depicting this scene still stands proudly in Sleepy Hollow. We also learn about the Van Tassel family, whose daughter was the inspiration for Crane’s love, Katrina Van Tassel. Our favorite horseman was taken directly from a Hessian soldier who literally lost his head from a cannonball shot during a Revolutionary War battle. 

The search for other Sleepy Hollows takes Ocker across the country, where he finds towns with that name in states like California, Wyoming and Illinois. There is a well-known bar in Las Vegas of all places called Ichabod’s Lounge. There also have been countless films and television shows inspired by this story --- from Tim Burton’s Sleepy Hollow to the recent FOX series of the same name, as well as a myriad of cartoons. Perhaps the most famous of all is the brilliant Disney animated short film, sung and narrated by Bing Crosby, which gives us the best depiction of Ichabod Crane and the Headless Horseman. It inspired Sleepy Hollow eateries in Disney theme parks, and the Headless Horseman leads the Halloween parade each year at Mickey’s Not-So-Scary Halloween Party. I still get chills every time I see it!

The book wraps up with Ocker and his family enjoying the Halloween celebration in Sleepy Hollow, an extremely popular month-long event where parking is at a premium and activities spread outside of the town into the surrounding areas amidst the beautiful Hudson Valley. CHASING THE HEADLESS HORSEMAN shines a light on a tale that has taken on a life of its own --- and in doing so has embedded itself into the culture of our country and the Halloween season forever.