In 1993, Trail won the Kentucky State High School Tennis Championship as a 7th grader.

6 in the ITF world junior rankings, represented the United States in the Connolly Continental Cup, was a member of the USTA's Team USA, and was the recipient of the Maureen Connolly Brinker Award.

she advanced to the semifinals of Junior US Open, defeating Justine Henin in straights sets in the quarterfinals.

Later that year, Trail signed with Octagon sports agency and turned professional.

In 1998, she again advanced to the second round of the US Open, narrowly losing to Wimbledon champion Conchita Martínez.

Trail continued to play on tour the following few years through her increasing number of injuries.