Saint Jo is the oldest town in Montague County, Texas and from 1849 until 1873 it was known as Head of Elm.

Government records in Washington, D.C. reveal that Captain Randolph B. Marcy camped at the springs at the head of Elm Fork of the Trinity with his surveying crew in 1849. Captain John Pope and his men camped there in 1854 as they surveyed for a proposed federal railroad across the county from Arkansas. The Civil War later resulted in cancellation of the building program.

The U.S. Second Calvary out of Missouri under Colonel Albert Sidney Johnson camped at Head of Elm in 1855 in route to establish frontier forts in West Texas. His journal makes reference to the area.

In 1857 Colonel James B. Leach led the government "Corn Trains" to Fort Belknap with supplies for the soldiers stationed there. His official journal refers to the frontier settlement here as the last west of Gainesville.

The first settlers to arrive in the area now known as Saint Jo in 1849 were Ithane and Prince Singletary. They were said to have been looking for gold. They settled about one and one half miles south of head of Elm Creek. Shortly they were joined by a John Hughes family. They were disappointed when they found no gold and moved to Whitesboro. About two years later the Singletary family moved back and settled what is now Saint Jo, but called it Head of Elm.

Little is known of the town between 1858 and 1870. It was one of the voting places when the county seat was selected and the county organized, It was one of the sites considered, but the voters favored the Montague site in the center of the county. This was a time of Indian raids, most often Comanche. Stories of the raids (and sometimes artifacts of them) are found in and around Saint Jo. The gravestone of a local citizen, James Harris, noting his death at the hands of Indians in 1866 after having served in the Confederate Army, is plainly visible in a small private cemetery on the northeastern edge of town.

Among the pioneers who arrived at Head of Elm in 1869 was Captain Irb H. Boggess who was born in Tennessee November 5, 1835. He had served with the Confederate army during the Civil War. Other settlers arriving about a year later included the Meador and Pedigo families from Tennessee; the A.H. McLane, Jasper Field, W.N. Bellah, I Chancey and Howell families.

From 1867 to 1870 Head of Elm was the last stop in Texas to the cattle herds that were on their way up the Shawnee/Arbuckle Cattle trail to the newly founded cattle town of Abilene, Kansas.  In 1871 the Old Chisholm Cattle Trail was born.  This historic cow trail is said to have as many as five million Texas Longhorns travel its route from South Texas by way of Fort Worth and Saint Jo crossing at the famous Red River Station Crossing in route to Abilene, Ellsworth, Newton, Wichita and finally Caldwell, Kansas. Saint Jo played an integral part of the great cowboy legacy born during the historic days of the “Wild West”.

In 1871 there were seven stores in the village. Five of the stores sold whiskey and there was a post office and blacksmith shop. Merchants hauled their goods from Jefferson, Texas, and Shreveport, Louisiana, by ox wagon.

In 1872 Captain Boggess and Joseph Anderson Howell formed a partnership and purchased 640 acres of land from the Alex Kitchen Survey. That year Boggess began the erection of the first permanent building to house his Stonewall Saloon. This establishment served drivers on the Chisholm Trail as they moved cattle north to the rail head at Abilene, Kansas. The Stonewall Saloon building still stands, having been restored as a museum. A bar well over a hundred years old is still inside. A rooming house was on the second floor, and stories differ as to what pleasures were available to cowboys staying there!

In August 1873 the town promoters laid out the present townsite, encompassing much of the original village of Head of Elm. Some say they used a grapevine and followed a Spanish compass with the streets running southeast to northwest and southwest to northeast for one-half mile in each direction from the square. It is said that the promoters laying out the town were so impressed by the abstinence from alcohol of a surveyor named Jo that they named the town Saint Jo. (A more scandalous version of the story is that Jo was tempted by alcoholic spirits so often that the town was so-named in jest!) 

Reverend James Anderson of New York state arrived in Saint Jo in 1876 to become the first Presbyterian minister. He built the first church in 1878 and held the pastorate for some forty years before going to Bowie to help establish the Presbyterian church there.

A well-known descendant of Joseph S. Howell, Donna Howell-Sickles, grew up on a ranch near the Red River some twenty-five miles east of Saint Jo. Her paintings of vibrant cowgirls have been eagerly sought by museums and collectors all over America. Today Donna and her husband John have an art gallery on the square in an old building that they renovated.