Pilot (Pilot's) Point was at the junction of U.S. Highway 377 and Farm Road 455, eighteen miles north of Denton in northeastern Denton County. The Missouri Pacific Railroad tracks ran through the community, and Lake Ray Roberts was immediately to the west. It was named for its location on the top of a ridge that could be seen from a distance. The grove of oak trees with one tall cottonwood in the center was used as a landmark by Indians, Texas Rangers, scouts, and early settlers. Dripping Springs, just north of the hill, provided water and a convenient camping area for travelers and was an attractive area for settlers as early as 1845, two years before the county was organized. The land was granted to Charles Smith's heirs on March 13, 1841. James Pierson laid off the plat of Pilot Point on February 11, 1854. Settlers arrived rapidly, and Pilot Point received a post office in 1855 with James D. Walcott, the owner of Pilot Point's first general store, as postmaster. In 1856 the first subscription school in the community opened, operated by a New Yorker, Alphius "Yankee" Knight. Two churches were founded that year, the First Baptist and the Methodist. In the late 1850s the Butterfield Overland Mail stage route ran through Pilot Point.
On July 8, 1860, Pilot Point was one of ten communities, including Denton and Austin, which had a fire blamed on a Black uprising. The fire in Pilot Point caused $10,000 damage. During the Civil War the men of Pilot Point were active participants and organized their own Confederate company of 101 men under Capt. N. Wilson. The remaining inhabitants, because of their location near the frontier, were troubled by horse and cattle thieves. The residents formed a vigilante group, the Regulators, who meted out their own justice. Six cattle rustlers were hanged in one day from a large oak tree east of the community. One man, who claimed to be a former federal soldier, "Spoon" Butler, roamed the county stealing jewelry and silver spoons before he was hanged from a post oak near the square. After the Civil War Pilot Point continued its progress, which had been halted by the war. On October 8, 1866, Pilot Point was incorporated. During Reconstruction violence in the community made it necessary for nine policemen to be employed to keep order. In 1878 Pilot Point's citizens repealed their charter and were no longer an incorporated community. That year the first newspaper, the Pilot Point Post, was published by D. J. Moffitt and James Taliaferro Jones.
Education continued to be available only by subscription. In 1872 two schools in the community were consolidated as the Pilot Point Seminary, later renamed Franklin College for one of its founders, Dr. M. B. Franklin. The school was officially chartered in 1884 and offered education from elementary to college education, with a bachelor of arts degree available. A public school opened in Pilot Point in 1894, and Franklin College closed in 1900. The campus was purchased by the Holiness Church in 1901, and a church and orphanage operated on the school's campus. In 1903 Rest Cottage, a home for unwed mothers, was established.
Pilot Point became more accessible to the outside world in the 1870s. The military built a telegraph line from Sherman to Jacksboro in 1877, running the line through Pilot Point. The road that ran beside the line became known as the Wire Road. By the 1880s two railroads had come through the community, although it had only one track. The Texas and Pacific Railway arrived in 1880, and the Missouri, Kansas and Texas leased its track. Before this time supplies were shipped by oxcart from Jefferson. In 1890 Pilot Point was a thriving community with a population of 1,090. Many businesses served the community, including the Pilot Point Bank, which was chartered in 1884, a roller flour mill, several cotton gins, the Pilot Point Post-Mirror (a weekly newspaper), blacksmiths, gunsmiths, a saloon, a grocer, a hardware store, a meat market, a hotel, Waters-Pierce Oil Company, a jeweler, and a restaurant. The railroad shipped cotton, grain, and hides.
A major influx of new residents was brought in by the Flusche brothers in 1891. Emil Flusche, a Catholic empresario, and his brother Joseph along with a local land owner, J. M. Sullivan, published promotional literature encouraging German Catholics to settle in Pilot Point. Emil had founded other colonies, including Muenster, Texas, and colonies in Iowa and various other states. The Germans were urged to attend the newly completed St. Thomas Catholic Church, which held its first mass on November 4, 1891. A parochial school was opened in 1893 in the room above the chapel. On the first day of school fifty students registered for the classes up to fourth grade level taught in German and English by two nuns. By 1901 the enrollment was eighty. Later a new church was built, and a separate school was built in 1917, when the old one burned. The church and St. Thomas School remained active into the 1990s.
Pilot Point continued its growth, and by 1906 it was reincorporated. The population was 1,371 by 1914, and services were supplied by Pilot Point's own electric plant and water works. There were also a creamery, an ice plant, three banks, and seven churches of three denominations. The German influence could be seen in the formation of a German band. The newspaper was called the Pilot Point Post-Signal, and it retained that name for the remainder of the century. The population rose slightly in the 1920s, but by the 1930s it dropped to its pre-1900 level of 1,108. At that time the community had forty-five businesses, including the Pilot Point Refining Company. By the 1950s Pilot Point had 1,156 residents and sixty-five businesses, including two lingerie manufacturers and a manufacturer of church and school furniture. It had a population of 2,538 in 1990. The community had its own library, three public schools with an enrollment of 865 students and sixty-two teachers, twelve churches, and two municipal parks with baseball diamonds and soccer fields. It had three banks and ten manufacturers, including cabinet and counter manufacturers, irrigation equipment makers, equestrian supply, and clothing manufacturers. State historical markers honored the Pilot Point Church of Christ, the Pilot Point Post Signal, and the city of Pilot Point. The population was 3,538 in 2000.