Rides | Hinckley Loop (South Portland)

The Hinckley Loop in South Portland offers a decent ride, but you need to know where to make the links to other trails. Start at the Hinckley Park parking lot and follow the trail to the park perimeter, which ends at the gate. Turn right onto Stillman St. and then take your first left onto Pilgrim Rd. Proceed down the street for appr. 1/2 mile until you see a trail on the left that leads in to the woods. Bear right about 50 feet into the woods. Ride the singletrack trail through the "Log Park" and take the doubletrack to the powerline (bearing left on the PL). Cross Fickett St and ride the powerline for about 3/4 mile, cross the little stream (may be dry late in the season) to the steep climb on the other side. At the top you can go straight (easier) or look for the partially hidden route over exposed rock with a fallen tree across it (known to Rage as "The Hillbilly Highway")- either way you'll come to a doubletrack jeep road. Bear right (don't go left or an angry landowner will chase you down his driveway!) and cruise down the jeep trail to an "S" turn and look for the singletrack on your left. Follow that for about 1/2 mile until you come out onto Prouts Place, an upscale neighborhood with big houses! Go up the road and at the bend head up the trail on the left. You will cross Fickett St. after about 100 yds. Go straight across and ride the "whooptie" to the next section. OK, we got you this far, there are many trails and route variations here. Print the map below and go explore! The major trails are the Power Line and the doubletrack Snowmobile Trail with many marked "greenbelt" trails off of them. When you're done here, head out to Sawyer St., turn right and ride straight onto Fickett St (Sawyer bears right) back to the powerline and backtrack to Hinckley Park. Another option is to ride out the back of the "Greenbelt" section, ride the road for a couple of miles and ride the Shore Road Trails.