Pilot Point has from its founding been a place that seemed restful and relaxing to people as they came by where Pilot Point is located. As early as 1845, two years before Denton County was organized settlers began making their homes near the "Pilot's Point," situated on the edge of the Cross Timbers Section of Texas. These settlers had migrated form Arkansas, Tennessee, Kentucky, and Missouri to establish themselves on either the rich, endless black land prairies of the east or the expanses, of sandy wooded land to the west.

The highest point of land in the area was a small hill on which the city square is now located. Oak trees covered much of the hill. Standing tall above the oaks was a magnificent cottonwood tree that could be seen from a great distance. This high, wooded point of land was a landmark for the Indians and later for rangers, scouts, and other travelers guiding them across the sprawling trackless land. The landmark became known as Pilot's Point. Gradually the name was changed to Pilot Point. A short distance to the north was Dripping Springs, which provided excellent water and a pleasant campground.

The spirit of progress and the desire for orderly development was present in the people of Pilot Point. In 1872 the Pilot Point Seminary was established. It attracted local students as well as those living outside the area. It was a fine institution of learning. In 1892 the name was changed to Franklin College, an outstanding subscription school with fifteen teachers serving primary grades through college. The birth of public schools in 1894 led to the gradual decline of enrollment at Franklin College, which operation in 1900.

Pilot Point was on the route of the Butterfield Stage, which brought the mail. In 1877 the first telegraph lines came through. It ran from Sherman west through Pilot Point along "Wire Road," which is now known as FM 1192. The telegraph line extended to a government post at Jacksboro. Pilot Point's first telegrapher was Ed Reaves. He was the son-in-law of the former Governor Throckmorton, and later was the chief telegrapher at the White House.

Using brick made locally, John Merchant in 1872 erected on the northeast corner of the square, the first brick building in Denton County. Soon all the businesses and houses around the square were replaced with brick buildings.

The town's first newspaper The Post appeared on August 31, 1878. The Post's successor, through several consolidations through the years, was The Post-Signal. It still covers the news of Pilot Point and surrounding areas.

In the autumn of 1880 the first train rolled through Pilot Point over the newly constructed line of the Texas and Pacific Railroad. Under a lease arrangement the Missouri, Kansas, and Texas railway ran over the same track. This gave pilot point excellent passenger and freight service for many years. A cotton gin was built by Henry Selz and J.P. Cooper. It was the largest gin in the United States at the time.
The first bank in town was privately owned. It opened in 1884,and eight years later it became the Pilot Point National Bank. The bank continues to serve Pilot Point today, but is now know as Point Bank.

The early years of the 1900's found Pilot Point humming with activity as a marketing center for farmers and stock raisers who experienced good as well as bad years. By the 1920's Pilot Point had fifty businesses, three banks, nine churches, a free public schools system, a hotel, two federated women's clubs, several fraternal organizations, one being the Masonic Lodge A.F. and A.M. chartered in 1862. the local Masonic Lodge is one of the oldest in Texas.

Soon after 1900 the buildings formally known as Franklin College were purchased by a local business man named Rogers. He was approached couple named Roberts, that was interested in the welfare of children and expectant mothers. In 1904 an orphanage was opened, and in 1907 a home was established for unwed mothers. This place was called Rest Cottage. Rest Cottage was operated under a board of Rest Cottage directors, but managed by the Nazarene Church workers. In the following years the orphanage was transferred to another town, but Rest Cottage operated until 1971. When it was closed the records were sent to The Department of Human Resources in Austin Texas.

Pilot Point has always prided itself on good schools and a progressive city government. It is a delightful place to live, and is a very special town with an interesting history and a bright future.