The first Little Brown Jug Enduro was organized by the River Falls Enduro Riders in 1952. The club remained the River Falls Enduro Association until 1970 when the club name was changed.

The first Little Brown Jug Enduro was held in north Cleveland South Carolina. It was organized by David and Herman Brown. With their last names being Brown, they decided to call the enduro the Little Brown Jug. David and Herman laid out 125 miles of trail for the first race. A lot of the trail was laid out by driving around Rivers Falls in their car. About 40 riders showed up to ride the first event. Some of the first riders were Jim McCarson, Benny Boodle, Herman Brown, David Brown and Lowell Tankersley. Seven trophies were awarded to the riders. Ray Sang-Sing was the first overall winner of the LBJ. He was awarded a Brown Jug as his trophy.

The retiring of the trophy or Little Brown Jug is what sets the Little Brown Jug Enduro apart from all other enduros. To win this trophy you have to be the overall winner of the race. If the trophy is won, the winner has to bring the Brown Jug back the next year. To retire the Brown Jug, a rider must be the overall winner three years in a row. Ray Sang-Sing was the first rider to retire the Brown Jug. Other notable names to retire the Brown Jug are Ricky Weathersbee in 1978 and Randy Hawkins. Randy has retired the Brown Jug twice.

With the first LBJ being held in Cleveland, SC, the event has been held in many different locations over the years. Some of the other locations were Jones Gap, Matthews Creek, Glassy Mountain, Fall Creek and the River Falls Mountains. Today the LBJ is held in the Sumter National Forest in Clinton, SC. The events today draw around 400 riders annually.