The following history is from Fannin County Folks & Facts:
On February 8, 1845, Anson Jones, as President of the Republic of Texas granted to Martin Moore five grants of 320 acres each south of Bois d'Arc Creek in Fannin County. These five tracts were contingent to each other and so situated that some part of the town of Leonard is situated on one or more of them. Martin Moore conveyed these tracts of land to Henry Sampton in 1851, who in turn conveyed them to E. J. Hart in 1853 for $4000. On January 22, 1859 E. J. Hart convened these tracts and other "totaling 3520 acres situated in Hunt and Fannin Counties to S. L. Leonard for $10,560 cash in hand paid for this and other land". Solomon L. Leonard died about the year 1862 or 1863 on his way from his holdings in Texas to his home in Buchanan County, Missouri.
In 1880 the Missouri, Kansas and Texas Railroad extended its line from Denison to Greenville and located a town on the martin Moore tracts owned by the Solomon L. Leonard heirs. The town was platted and named Leonard. A public sale of lots was conducted with a picnic and the annual Leonard Picnic was started.
The first lot was sold to Mark Daniels. It was located on the southeast corner of the square. In less than a week he had erected the first building and opened a saloon. H. L. Parmlee erected the second business, a general merchandise store located on the northeast corner of the square. In the same year the first hotel was built by John Mantooth. It was a two-story frame building located on the east side of the square and was later operated by Ed Groves, father of the late George Groves. The first blacksmith shop was erected near the northwest corner of the square, built by a man named Staley. His was one of the first graves in the cemetery. John Roberts bought the shop and operated it for a short time. He sold it to John Hickman under whose name it was operated over 75 years.
Over business establishments sprang up around the square: Allison and Grider Hardware, J. O. Kuyrkendall Dry Goods, G. W. Cund, J. R. Wilson Company which celebrated its 50th anniversary in 1938 and is the oldest business in Leonard. Thromas and Wilson Livery Stable, Thomas & Saxon Dry Goods, Denny Brothers Dry Goods, James Shiels Dry Goods, J. D. Albright General Merchandise and Billy Womack Grocery were other business establishments. By 1880 the principal trading center of the area was Valley Creek about 3 1/2 miles north of Leonard.
The Thomas Glade Baptist Church which became the First Baptist Church, the Valley Creek Presbyterian which became the First Presbyterian Church and a Methodist Church from the Delba community became the First United Methodist Church moved to Leonard in the 1880's. The predecessor the Leonard Church of Christ was Macon's Chapel, located about three miles east of the new townsite and moved to Leonard in the 1900's. Also moving from Grove Hill in 1882 was Grove Hill Lodge No. 373 A. F. & A. M.
In 1885 the town of Leonard was incorporated. The city limits extended 1/2 mile east, south, west and north from the present city square. By the early part of the 20th century Leonard was a thriving town with several cotton gins, an oil mill, a flour mill, a bottling plant, four dry goods stores, three banks, four doctors and a college. An unusual business in Leonard during this period was F. N. Rigney & Company, which operated peddling wagons as far as 15 miles away. This firm sold dry goods, notions, groceries and what-have-you. They bought chickens, turkeys, eggs and butter from the farm wives.
The first City Hall was located downstairs in a two-story frame building situated in the center of the square. The Grove Hill Masonic Lodge occupied the second floor. A two-story brick building was erected in 1909 on the square and housed the City Hall, fire station, a meeting room and the post office downstairs. An auditorium occupied the second floor. This building was replaced in 1964 by the present building.
The photograph above and those below from Steve Coker. The photo above is the west side of the Leonard square looking northwest taken during WWI. The Rock Hotel and the Woosley hardware building (left) burned in 1943.
The photo below is the northwest corner of the Leonard square looking northwest, including the first courthouse, about 1904.
Leonard has a wonderful historical museum on the town Square with many photos. For more history, see The History of Leonard, Texas, Volume II, for sale at the Museum.