Posted on March 5, 2018 and last updated on September 28, 2026

Messalonskee School Trail

Oakland, Kennebec County

QUICK TRAIL FACTS

  • Preserve Size: not sure
  • Trail Mileage: ~1.2 miles
  • Pets: no
  • Difficulty: easy
  • Sights: pine grove, pond, school fields

This trail system makes an easy loop in the woods (Eagle Trail) behind the high school. It’s quiet and peaceful and might see fewer walkers than other area trails because it does not allow dogs. The Eagle Trail overall is well maintained, though the Fox Trail might be a bit overgrown in the summertime.

The trails closer to the middle school are a bit scruffier than the Eagle Trail, but they also offer a few sights: a little retainment pond with benches placed around it and an outdoor classroom, with more rustic benches.

KM Trails is a great source of information for local trails.

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.

Let me know if you have any trail updates or corrections!

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