Brom Bones later became the inspiration for the character of Gaston in Beauty and the Beast (1991).

When shown on American television in 1977 shortly after the death of Bing Crosby, the end credits included a frame noting his passing and contribution as narrator/singer.

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

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.

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 Chernabog 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 visual aesthetic and slapstick comedy of the film were heavily influenced by The Headless Horseman (1922) starring popular humorist and entertainer Will Rogers. The original character sketches of Ichabod Crane were exaggerated caricatures of Rogers' hatchet-face.

The church shown during the opening narration ("...and yet somehow foreboding") and where Brom & Katrina get married at the end is drawn to look like the actual Old Dutch Church in the real Sleepy Hollow that was built in the late 1600s and still stands there (and is still used during the summer).