- In 1997, the village of North Tarrytown, New York, where many events of the story took place, changed its name to Sleepy Hollow. The high school teams are named "the Horsemen".
- In 2006, a large statue depicting the Headless Horseman chasing Ichabod Crane was placed along Route 9 in Sleepy Hollow/Tarrytown, New York.
- Since 1996, nonprofit organization Historic Hudson Valley has held "Legend Weekend", an event at the Philipsburg Manor House in Sleepy Hollow, featuring a rider portraying the Headless Horseman and a storyteller retelling The Legend of Sleepy Hollow as a historic celebration attended by thousands annually before Halloween.
- Town and village names:
- Sleepy Hollow, Illinois, many of the street names reflect characters from the tale, and the image of the Headless Horseman can be found on many of the city's landmarks and publications.
- Sleepy Hollow, Marin County, California, has Irving Drive, Legend Road, Ichabod Court, Katrina Lane, Van Tassel Court, Baltus Lane, Crane Drive, and Van Winkle Drive.
- Subdivision names:
- Bethel, Connecticut, "Sleepy Hollow Estates", Ichabod Lane, Legend Drive, and Katrina Circle.
- Roanoke, Virginia, and Longwood, Florida, "Sleepy Hollow", street names such as Ichabod and Horseman.
- Pearland, Texas, "Sleepy Hollow", street names such as Washington Irving Drive, Sleepy Hollow Drive, Crane Drive, Tarrytown Lane, and Brom Bones Boulevard.
- Port Jervis, New York, Sleepy Hollow Road
- Falls Church, Virginia, Street names Sleepy Hollow Road, Crane Drive, Ichabod Place, and Horseman Lane. There is also a Sleepy Hollow Park and Sleepy Hollow Bath & Racquet Club.
- Mt. Lebanon, Pennsylvania, Sleepy Hollow Road
- Spinnerstown, Pennsylvania, Sleepy Hollow Road
- Hampden Township, Pennsylvania, "Sleepy Hollow", Ichabod Court, Brom Court, and Katrina Court.
- State Parks:
- Sleepy Hollow State Park, Laingsburg, Michigan
- The Ichabod Crane School District, Valatie, New York. The school's sports teams are called "The Riders" and a silhouette of Ichabod Crane on his horse is often representative of the home team while a silhouette of the Headless Horseman is representative of the opponent. The wings in the junior high school are also named for characters and places, such as Katrina Van Tassel and Sleepy Hollow.
- Sleepy Hollow Elementary
- Orinda, California, has Washington Lane, Sleepy Hollow Lane, Tarry Lane, Van Ripper Lane, Van Tassel Lane, Tappan Lane, and Crane Court.
- Pinson, Alabama's Sleepy Hollow Subdivision has Sleepy Hollow Drive
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