The first running of the Ouachita Trail 50 was on May 13, 1989. It was called the Long Crossing: 50 Miles on the Ouachita Trail. The Race Director was Teresa Laster, and the Big Shot was Assistant RD. Tom and Tammy Chapin, Bill Laster, Otis Edge, Lou Peyton, and Nick and Sharon Williams also assisted with the organization. It was aptly named by the Big Shot to reflect the long distance runners would have to travel between the North Shore Aid Station and Hwy 113 (8.3 mi1es).
The following year, the name was changed to the Ouachita Trail 50 and the race was directed by Bill and Teresa Laster. They continued as race directors until 1993. The race was in jeopardy of not happening in 1994 until Nick Williams took it up as a low key, no entry race. In 1995 and 1996 Bill and Teresa returned again as race directors, putting on a low entry, limited aid race. In 1997 Nick again administered it as a no entry, low-key event.
Sadly, there was no Ouachita Trail 50 in 1998 or 1999.
In 2000, Ann Moore resurrected the OT50 as a full-fledged race, adding the 50K distance. One night after having several margaritas, Chrissy Ferguson agreed to replace Ann as race director, so she and Stan began directing the race in 2001. They made the 50K distance a little longer. For 2002, the bright idea was hatched to utilize trails going over Pinnacle Mountain on the "out" route, making both races a little longer (and tougher). For 2003, a full loop over and around Pinnacle was incorporated--lengthening the routes again to the current version of the course.