It grew in the 19th century at the intersection of several military and trade roads and was an important crossing on the Shawnee cattle trail.

Preston lost prominence after the MK&T railroad bypassed the town to the east, leading to a decline in traveler and cattle drive traffic.

[2] Before European settlement, the general area of Preston had been occupied by the Caddo people, with the Comanche and Kiowa farther to the west.

One of the first American settlers in the area was John Hart, who cultivated land at the bend in the Red River possibly before 1826.

[12] Roughly following a much older trail used by Native Americans for centuries, in 1840–1841, Colonel William Gordon Cooke created the military road from Coffee's trading house on the Red River to Austin.

[12] When Holland Coffee married Sophia Suttonfield Aughinbaugh in 1839,[13] they resided at his trading post in a 100-foot (30 m) square log stockade on the Red River.

[9] In 1843, Coffee began building Glen Eden as a proper house for his wife, 2 miles (3 km) west of his trading post.

[12] Rock Bluff Ferry operated near the mouth of the Washita River close to Preston.

[15] Preston was located on one branch of the California Trail, where it crossed into Texas from the Indian Territory.

This plan was abandoned in 1853 due to the difficulty of navigating the upper Red River because of the Great Raft logjam.

Although Preston developed as the largest community in the area for many years, several factors led to its decline.

The Butterfield Overland Mail stage route, between St. Louis and San Francisco, began operation in 1857.

The line ran across the Indian Territory from Fort Smith, Arkansas, to the Red River at Colbert's Ferry, a few miles east of Preston.

The stage line had decided to bypass Preston as the traditional crossing on the Red River.

[5] Colbert's Ferry became a more popular crossing over the Red River as Sherman and McKinney developed.

This railroad, the Missouri, Kansas and Texas, crossed the Red River near Colbert's Ferry to the east of Preston in 1871.

[13] In the 20th century, Preston had a public school system, two churches, a cotton gin, and a cemetery.

The United States Army Corps of Engineers bought all the land in the area in the late 1930s for Lake Texoma.

[13] After the filling of Lake Texoma, only the cemetery was left from Preston; which was on high ground overlooking the town.

An unincorporated community named Preston exists on this peninsula, consisting largely of campgrounds and recreational cabins.

This area is located a few miles east of the Cross Timbers on the upper Red River above the former Great Raft logjam.

Later, the bluff also marked the return route of Captain Randolph B. Marcy's expedition from Santa Fe to Fort Smith in 1849.

Texas State Highway 289 has its northern terminus in Preston and leads south 7 miles (11 km) to Pottsboro.