Messalonskee School Trails - Oakland & Oakfest

This pleasant woodchip and gravel-lined trail loops around the edges of the Messalonskee Middle School and High Schools. It's fairly well-marked, with signs denoting the trees along the pathways (from maples to birch and evergreens). We'll pass through some patches of tall grass, including the Eagle Trail, which loops around and back through the ball fields.

There are also some slight inclines during the first third of the trail.

We can extend the walk by checking out the nearby Oakland end of the Kennebec Valley Trail or by walking through Oakfest. OakFest offers live music, classic cars, food trucks, and other vendors. If we feel up to it, afterward, we can buy brunch from one of the vendors.

Please see the attached photos for more details -- including shots of classic cars from the festival three years ago.

Trail walk length: 35 to 40 minutes at a moderate pace.

Where We'll Meet: In the parking lot behind the rectangular gray and brick Messalonskee Middle School near the field -- past Oakfest, which will take place at the Elementary School (brick building). Look for the green and gold "Trails" sign. As pictured, colorful metal signs are on the field near the trails.

Per the town clerk, if the parking lots are full, it's OK to park on the street in front of the Elementary School.