The town has always had a post office, though for many years it was located in one of the general stores with the clerks acting as postmaster. If the store was sold the office went to the new owner. It was housed in many different places through the years. The mail arrived by train. In early days when the mail came in people would flock to the post office. One whose name was called would answer, “Here”, and his mail would be tossed to him. One day the postal inspector unexpectedly visited the office, and this method of handing out mail was not used again. 

The post office was in the Dan Curtright store from 1898 to 1902. From 1902 to 1905 it was in a store run by H. R. Blades. It was then moved to a brick building on the east side of the Main Street where it was run by J.M. Blades. It was later moved to another location, still under the James Blades name, but operated by his daughters, Maude and Ruth. 

In 1914 Guy Brooks became postmaster. He was succeeded by Tom Sparks in 1921, who held office until 1933. In both cases the location was again changed. Mrs. Ben Glasscock became post-mistress in 1933. The office was then in the present Masonic Lodge building, but later moved to a room in the rear of the first floor of the present Odd Fellows Hall, and still later to the Monroe County Exchange Bank building. It was located there when the building burned in 1959. Temporary quarters were then set up in the basement of the Justus Olney home, and remained there until the building which now houses it was constructed. Mrs. Glasscock retired as postmistress in 1960. Mrs. Jane Callison was appointed as temporary postmistress, and retained the position until Lee Mitchell was appointed in 1961. He continues to serve at this time. His assistant is Mrs. Lois Blades.

 The first rural mail route out of Holliday was started in 1901. Grundy Delaney was the first mail carrier. All rural boxes at that time had locks on them. At one time there were three rural routes. Carriers have been Will Blades, Elwood Curtright, J. A. Hemmings, J. B. Weldon, Eldon Hess, Herbert Halliburton, and Justus Olney. At present all former mail routes have been combined into one, and Justus Olney is the carrier.