William Wall opened a store on this site in 1842, and in 1874 a U.S. post office opened in his store, after which the area became known as Wall's Crossroads. The original store later burned down, and the current building was erected in 1905. The post office remained in this building until 1973, when it moved across the street to a trailer, and it moved again in 2003 to its present location on Highland Road. The second postmaster was Charles T. Disney, son of Joshua E. Disney, the wheelwright, and he changed the name of the post office to Highland. Local legend holds that the highest elevation in Howard County is in this area at Allnutt Farms on Highland Road. Charles T. Disney served as postmaster for 33 years.