In earlier days Holiday was a prosperous thriving town, and many businesses and industries developed through the years.

In the days before the automobile there were many horses and carriages; therefore, there were blacksmiths. One stood near the area where the Callison Feed store has been built; another back of where Mac Donovan’s building now is, and a third on the location of the present Smith Welding Shop. It is believed that Sam Tedford was the first smith. Others were a Mr. Kenney, Everett Bristow, Tyler James Durbin, a Mr. Milligan, Bob Holder, and Tom Furnish. The Smith Welding Shop was operated for many years as a blacksmith shop and garage by Earl Smith and his son, Harry, who is the present owner and operator.

 Another important building in the horse and buggy” days was the livery stable, which stood facing the south on a lot west of the present Masonic Lodge building. This was operated at various times by a Mr. Hall, Theo Webb, John Farrell, Will and Lon Blades, and Jake Heathman and Lewis Hobson, who were the owners when it burned in 1923.

 The Blades Brothers owned horses, buggies, and carriages which they rented to people who wished transportation. They provided teams and dray wagons for unloading shipments which came in on freight trains, and for moving heavy articles and commodities for the townspeople.

These were the days of the “drummers”, traveling salesmen, who came into town by train, bringing with them large trunks containing merchandise to be sold to the merchants. Quite often the livery stable provided, not only the horse and wagon, but also a driver, as these drummers made their calls to area stores. A horse drawn hearse was stored in the livery stable, and horses from the barn were used to pull it when needed. In the early nineteen hundreds the Blades brothers built a training barn, which still stands south of the schoolhouse. Here people brought saddle and harness horses to be trained and schooled. Many came from out-state areas. These were show horses, and were often taken to fairs, traveling by train, in cars equipped with stalls. Carts, saddles, and buggies were also transported by train. The land on which this barn stands is now owned by Gene Carter.

 There have been two hotels in the town. The first one was a large two-story structure built in 1879 on the east side of Main Street on the lot where the grocery store now stands. This was operated at various times by such families as the Burtons, Singletons, Brooks, Mattersons, and the Rice sisters. This building was destroyed by fire in 1902. Another hotel was built by Bailey East in 1903 on the corner lot north of where the Masonic Lodge building is now located. It was run at different times by East, Steve Overfelt, George Dry, Minnie Jackson, and Dave Delaney. This building was also destroyed by fire in 1890.

 In 1887 a large grain mill, with a mill pond, was erected by James, Henry, and Sam Blades. It was located in the west part of town on land where Mrs. Theresa Molluer and Earl Blackaby now live. It burned to the ground in 1890.

Tom Gaines and a Mr. Brewer ran a lumberyard in early days, located west of the Callison Feed Store. Later it was run by Thompson Moore. ln the early 1900’s a lumberyard was built by J.C. Frank, of Madison, and was run by E.W. Hobson for many years. This was on the lot between the present grocery store and the railroad track. In 1936 this building was bought by Ralph Howe, who set up a feed and produce store, a mill, and a coal business. This was operated until 1948. About one-fourth of the original building still stands, and is used by Guy Callison as a storage building.

 One of the first furniture stores and undertaking departments was owned by E.T. Sanner and Bob Atkinson. It was sold to l.A. Wilson, then later to Elton Miller, who ran it until 1920. It was then taken over by Fred Thompson, who owned it until it burned in December, 1932. After that Mr. Thompson maintained a funeral parlor in the home now occupied by Herbert Halliburton, with Mr. and Mrs. Newt Turner, and later, Mr. and Mrs. Charles Glasscock, acting as caretakers. The funeral parlor was later moved to the home of Mr. and Mrs. Boyd Curtright in the house where Gary Menefee now lives.

 The first drug store was owned and operated by Sam Moore. At one time there were two drug stores, one owned by William McCann and one by Holliday Arnold. These were combined into one store around 1913. After that the drug store was operated at various times and in various places by Marvin Dooley, Bob Harrell, Al Curtis, Paul McCann, and a Mr. Armstrong. Often a pool hail was run in connection with the drug store.

 In its time of greatest growth the town maintained as many as four grocery stores. These have been operated by Henry Blades, who ran one for thirty years; James Blades, F.G. Davis, Henry Henderson, R.C. Udell, Chester Atterbury, Charley Spears, Bailey East, M.B. Church, D.B. Chapman, D.L. Curtright, Boyd Curtright, Tom and Jim Jones, Lewis Curtright, Ray Wilhoit, Cloyce Menefee, Jimmie Dickerson, Benton Dickerson, Ben Durbin, Richard Phillips, William Hayes, Bob Winterbower, Ralph Howe and Pat Hartman. These were owners prior to 1959, and the stores were operated at various locations. For many years a grocery store building was located on the lot between the Burnett Repair Shop and the Donovan building. In January, 1959 this building was destroyed by fire. The store was then being operated by Bill Appieman. The present building, which houses the grocery store and the post office, was built by the Holliday Christian Church in the summer of 1959. Those who have operated the grocery store in this location have been Bill Appleman, Cloyce Menefee and Delbert Secoy. At present the store is run by Roland Norman.

 Hardware stores have been owned and operated in the past by Harve Thomas, Fletcher Overfelt, Henry Blades, John Wilson, Harry Curtright, Will Curtright, Willis Cunningham, Mac Donovan, and Forrest Menefee.

 Barber shops in the town have been run at various times by l.A. Hemmings, Jack Hackey, Roy and Bob Evans, Bounds Horn, Baxter Overfelt, and Ben Foster. The barbers were called “tonsorial artists” in early day advertisements. 

A millinery shop was once run by Mrs. Hess Jackson. A general merchandise store was owned by Hamp Solomon. John Phelps was a chair maker, and ran a shop in his home, the house now owned by Clarance Johnson. Later, Elmer Turpin made chairs in his home in the north part of town. At one time there was a saw mill, hoop and stave factory in the area.

 In 1919 a grain elevator was built near where Sadie Maude Jackson now lives. it was owned by a Farmers’ Co-Op. Holliday lies in a grain-producing area, and the elevator did a thriving business. This building was later torn down.

 Holliday has had two banks, the Monroe County Exchange Bank and the People’s Bank. These were later combined into one organization. This closed during the depression of the thirties.

 In the 1940’s a hatchery and broiler plant was owned and operated by Ralph Howe in a building which stood south of the present grocery store. He later moved this business to his home in the south edge of Holliday. This was closed in 1960.

 With the coming of automobiles, garages became necessary. One was run by the George Holsheiser family for a number of years in the building formerly occupied by the Cumberland Presbyterian Church. This burned in the spring of 1932. It was replaced by the brick building now known as the Odd Fellows Lodge Hall. The garage occupied the lower floor, and the lodge meetings were held in the top floor. In 1944 Mac Donovan took over the garage, and, assisted by Justus Olney, ran it until 1964, when he moved his business to its present location on Highway 24 east of Holliday.

 The newest business in Holliday is the Callison Farm Service Center established in 1963, and owned and operated by Paul and Guy Callison. This is a feed and fertilizer plant, and is a thriving and growing business.