[5] Cross Plains was the first area of Robertson County that was settled by European settlers, with the arrival of Thomas Kilgore in 1778.

In 1778, American Revolutionary War veteran Thomas Kilgore arrived at the Middle Fork of Red River, three-fourths of a mile west of Cross Plains, making him the first European settler to arrive in Robertson County.

In 2004, construction began on "Kilgore Park" located beside East Robertson High School.

In 2020, the Cross Plains city government announced that they had purchased 148 acres of land on Highway 25 west of Kilgore Park for $1.08 million.

City officials stated that the land was purchased for future uses such as an expansion of Kilgore Park, or new schools.

It provides an alternate route for local drivers to White House and Portland.

[10] In the late 19th century, two major stagecoach routes ran through Cross Plains.

The Louisville and Nashville Turnpike ran on the eastern end of town on the border of Robertson and Sumner County and the Hopkinsville and Gallatin Road ran through downtown and east toward Gallatin.

Beginning in 2021, the section of Interstate 65 became subject to widening to alleviate traffic strains.

[17] As of the 2020 United States census, there were 1,789 people, 689 households, and 513 families residing in the city.