The original town of Holliday was located one and one-half mile east of the present site, and was established in 1872. It consisted of a railroad station and a general store, operated by a Mr. Foster. It was called Foster’s Station. 

In 1876 the town was moved to its present location, on land given by Mr. William, Mr. John, and Mr. Thompson Holliday, and its name was changed to Holliday, in their honor. The southern boundary was at what is now the Smith Welding Shop; the east boundary was Main Street; the northern boundary was the lot now owned and occupied by Josie and Essie Durbin; and the western boundary extended to the Bethel Cemetery on the north side of the railroad track, but only to the Henry Soloman property on the south side of the track.

The first house was built on the lot where Josie and Essie Durbin now live. This was Lot #1, House #1. Other houses built at that time were on the lot where Chet Goldia now lives, the former Eula Ragsdale lot, now owned by David Farrell, and the lot now owned by Mrs. May Hughes. It is believed that the former Earl Smith house, now owned by Paul Rockett, is the oldest house in town.

The first store building was owned by the Holliday brothers, and stood on the lot where Oscar Burnett now has his repair shop. This store faced the north. These men sold dry goods and provisions, and did a prosperous business so that other enterprises were attracted to the location. Other stores were built west of this one. The proprietor of the second store built was C.C. Frae. In 1890 a fire destroyed most of these buildings. These were rebuilt. The Oscar Burnett repair shop is the oldest building in the town.

The town boundaries were enlarged by several additions of land. The first was in 1878, and was known as the Henry Glasscock addition. An addition in 1886 included the former J.A. Wilson property, now owned by Dennis Dickerson, and extended west to include the Charlie Overfelt property, now owned by Lloyd McCollum. A second Glasscock addition in 1888 extended the southern boundary to the south side of the Herbert Halliburton and Maude Hill properties. Another addition took the town to the northeast, to annex the land where Johnny Ragsdale now lives. In 1902 the James Blades addition was made. It was the lot on which the school building is now located. The properties of Clyde Ragsdale in the east part of the town, and those of Roland Norman, Leonard Carnes, Justus Olney, and Ralph Howe in the south edge of town were not made part of the city limits until the late 1950’s.

The house owned and occupied by Mrs. Ruth Curtright was built in 1901 by her father, J.M. Blades, and was the first house on what is now south Main Street. The second house was built in 1904 by Willis Cunningham, father of Mrs. Madge Curtright, and is now owned by David Menefee. Other houses on South Main Street built before 1910 are the Sam Akers and Ralph Howe homes.

Some of the early prominent families were the Hollidays, Williams, Fraes, Glasscocks, Welbans, Gwyns and Moores. Most of the people came from Kentucky and Virginia.

Holliday became a fourth class town in 1890. The first trustees were B. R. Wilson, James Brewer, William McDowell, S. D. McCormick, and S. D. Overfelt. In 1913 the town had a population of 400, and many thriving business establishments. Saturday afternoons were filled with activities. The merchants held drawings for prizes. At one time a Ford car was given as a prize. It was won by Mrs. Roy Houghton. Many business houses were destroyed by fires through the years and were not rebuilt; the depression slowed growth and the business section has declined, as has the population which is now 167.