Wolcott has injected the winning touch in each of his three high school stops, and his leadership with FC Frederick has elevated the level of girls' soccer in the area. He has been named local Coach of the Year four times, and he's been a part of high school programs that have won five state titles between 1997 and 2009.

As an assistant coach at Thomas Johnson for six seasons, he helped the Patriots to two state titles, four region titles and six county championships. He launched the girls' soccer program when Tuscarora opened in 2003, and in eight years had a record of 100-31-9, which included three state titles. With FC Frederick, more than 200 of his players have gone on to play NCAA Division I, II, or III soccer.