The show is inspired by fanfiction written by a young Sinead Persaud after seeing Il mistero di Sleepy Hollow (1999) involving Ichabod Crane and the Headless Horseman as roommates.
While the main characters (Ichabod Crane, Kat Von Tassel, Brom Bones, the Headless Horseman, Mr. Von Tassel, and even Douffe Martling) are from Washington Irving's short story "The Legend of Sleepy Hollow," other characters originate in other stories. Geoffrey Crayon, Diedrich Knickerbocker, and Jonathan Oldstyle were pseudonyms used by Irving. In particular, Knickerbocker narrated the "Sleepy Hollow" story and the story "Rip Van Winkle," which features the titular Mr. Van Winkle and (in the story) his daughter Judith Gardenier.
Blake Silver was meant to play Tom Walker (originally from Washington Irving's story "The Devil and Tom Walker"), but due to the COVID-19 pandemic and travel issues, Silver couldn't join the cast and his part was written out.
Jim O'Heir was originally cast as Baltus Van Tassel, but scheduling issues led to John Rubinstein playing the part instead.