Trekkers began in 1994 as a volunteer community initiative for students attending Thomaston Grammar School. In 1996, students from St. George School were included. During the first five years, Trekkers primarily worked with 7th and 8th grade students. With the expansion of a year-round program implemented in 1999, Trekkers began to offer programs to local students from 7th to 12th grades living year-round in the communities of Cushing, St. George, and Thomaston.
In 2010, the three communities Trekkers served were consolidated with Rockland, Owls Head, and South Thomaston to form a new regional school district. In the spring of 2011, Trekkers began offering its unique model of relationship building to all six of these communities. The organization completed its six-year expansion plan in 2016, which has increased overall student enrollment. Trekkers now serves more than 240 students in its core programs.