The trail was named by the Will Rogers Memorial Commission and dedicated on November 3, 1979, as a part of the Will Rogers Centennial Year Celebration.

Construction of the trail began in 1975 and was a cooperative effort between the Corps of Engineers and volunteers who were local members of the Oklahoma Equestrian Trail Riders Association.

The trail is continuous and was designed primarily for equestrian use, although hikers and mountain bikers are also encouraged to use it. Actual trail construction was held to a minimum so as not to disturb the natural features. The trail is delineated by fiberglass posts at appropriate locations. The trail is designed to prevent motor vehicle access. The trail wanders through open to dense stands of oak-hickory hardwoods connected by open pastures. It is moderately level, with the exception to the Tom Kight Hill portion of the trail of which sections are steep and considered a challenge to most equestrian riders (riders may choose to bypass this portion of the trail). One creek, near Blue Creek Park, must be forded to travel the total length of the trail. The total length of the trail is 18 miles, which includes 5 miles of random trails on and around scenic 346-acre Tom Kight Hill. Many species of aquatic wildlife, as well as wild turkey, deer, and quail, can be seen from the trail. The boyhood home of humorist Will Rogers can be seen northwest across the lake from several places along the trail.