The Devil’s Back Trail area in Harpswell, Maine, is another jewel managed by the Town of Harpswell. This rugged but narrow area straddles Route 24 on the way to Orr’s Island, with the east side overlooking Gun Point Cove, and the west on Long Cove. The Town of Harpswell has descriptions and a trail map here, and there is an excellent treatment of this hike in Maine Hikes off the Beaten Path.
The trails depart from a small parking lot, and contain matching butterfly wing or infinity loops (whichever comparison you prefer) on each side of 24, totaling about 2.5 miles (I take every side trail and viewpoint). I started to the east on a January morning, descending the winding and narrow path to immediate ocean views on the Gun Point Cove Loop. The path was empty, with only the sound of the crashing winter waves and I watched a variety of seabirds bobbing slowly up and down on the tide.
The Cliff Trail in Harpswell is an approximately 2.3 mile loop, with expansive views of the Long Reach, a long finger of a bay extending from Casco Bay inland. The popular trail, with parking at the Harpswell Town Office on Mountain Road, is well-marked and maintained by the town of Harpswell (see printable map and description here at town website). I started the white-blazed trail clockwise at sunrise on a mid-January morning. It was dark and a little muddy, with plenty of roots to trip over, but no snow had accumulated, and no traction devices were necessary. Strawberry Creek, to the west of the trail, narrows to a quiet, scenic cascade, and the trail turns inland.
Low pines and white birch bark lend an enchanted forest feel, with periodic fairy house “zones” adding to the effect on the way to the Henry Creek lookout. After this viewpoint, the incline of the trail begins, a series of switchbacks through rocks and mossy hummocks that takes you up and down the ridge of the eponymous cliff.