Trivia

While the characters are fictional, the place names and landmarks depicted in "The Legend of Sleepy Hollow" (1820) are mostly factual. The "Tarry Town" of the short story is the village of Tarrytown in Westchester County, New York. It was founded by Dutch settlers in the 17th century. It is located about 25 miles (40 km) north of midtown Manhattan in New York City. Some of the other landmarks are located in the nearby village of North Tarrytown, which was long nicknamed Sleepy Hollow and was officially renamed to this name in 1996. Washington Irving himself was buried in the Sleepy Hollow Cemetery.

Rat describes Toad's latest obsession as "Motor Mania". This is the title of a classic Goofy short which would be released the following year (Motor Mania (1950)).

The information that the Headless Horseman died in a nameless battle of the American Revolutionary War (1775-1783) is not unreasonable. The Province of New York was part of some major campaigns of the War and was the battleground for such battles as the Battle of Long Island (1776) and the Landing at Kip's Bay (1776). However, Washington Irving probably took his inspiration from the Battle of White Plains (1779), which took place only 10 miles from Tarrytown and Sleepy Hollow. An American General, William Heath, wrote in his memoirs that he witnessed a Hessian horseman being decapitated by a cannon ball during the battle. The body of the Hessian soldier was supposedly buried in an unmarked grave in the graveyard of Tarrytown's Old Dutch Church by the townspeople.

The Headless Horseman is often cited as being, along with the Firebird in Fantasia 2000 (1999), The Horned King in The Black Cauldron (1985) and Chernobog in Fantasia (1940), as one of the scariest villains in the Disney canon. Disney still receives complaints from parents about the character frightening their children.

The song "Headless Horseman" is considered one of the darkest songs written for a Disney film. Much like "Worthless" from The Brave Little Toaster (1987) and "Hellfire" from The Hunchback of Notre Dame (1996), it was nearly cut from the film.