Messalonskee School Trail, Oakland
Of all the trails I’ve done in the Waterville area, this is one of my favorites. It is well cared for (I guess by the students and teachers of the schools), it is well marked, with several maps set up throughout the trail system. The trail that makes a loop in the woods (Eagle Trail) is quiet and peaceful.
KM Trails is a great source for walkers.
Directions: You can park at either the middle of high schools. The trailhead kiosk close to the middle school and elementary school is set off across a field, at the edge of the woods.