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Devil's Back Trail Area
Devil’s Back: Two Woodland Ways to the Coast
Discover
Devil's Back Trail Area on Orr's Island offers two woodland loops with different coastal outlooks. Route 24 follows the ridge that gives the place its name, separating paths that descend toward Long Cove and Gun Point Cove. Choose a side before starting. The appeal comes from moving through trees toward water, with the narrow island's shape giving a modest outing a clear coastal identity.
The Town of Harpswell owns and manages the trails, and Harpswell Heritage Land Trust publishes visitor information. The parking area serves both sides, but reaching the western route requires a road crossing. Take that crossing deliberately and keep the two loops distinct when planning the return. A single side can provide a complete walk, while combining them adds another approach to the same island landscape.
On the western side, the route winds through mixed woodland before descending toward Long Cove. The manager identifies both older pines and surviving apple trees within that setting. Look at how an individual tree changes the scene around it, from the space beneath a tall canopy to the closer form of an old fruit tree. The woodland has interest between the water views, making the approach more than a necessary passage to the shore.
The eastern loop turns toward Gun Point Cove. Its outlooks provide another angle on the coast, with rocky shore and open water beyond the trees. Rebecca Goldfine's original account particularly enjoys opportunities to watch seals from this side, while noting steep sections and occasional rough footing. Bring binoculars if observation is the goal, keeping distance from resting wildlife rather than seeking a closer position along the rocks.
The two sides can also be compared through their views. A nearer branch can frame the cove, while a broader opening makes the opposite shoreline more prominent. Let the actual tide and weather shape what is visible. A rewarding visit does not depend on seals appearing or the water matching a photograph seen beforehand. The changing relationship between trees and coast remains a reliable theme for attentive walking.
Goldfine describes the trails as generally manageable but includes the descent toward shore among the more demanding sections. Use the current map and assess the group rather than equating a short loop with easy footing everywhere. The return climbs back toward the road. Give it time, especially after a long pause at the water, and remain on established routes instead of adding a scramble across exposed or slippery shoreline.
Follow current town dog rules, remove all waste, and leave plants and living shore organisms undisturbed. Camping and open fires are prohibited. For photographs, work from a suitable trail-side position and use the woodland as a frame for the cove. Return to the parking area with the chosen side's particular scene in mind: a sheltered western water view or the eastern outlook toward rocky habitat. Devil's Back rewards a visit that respects its small changes in terrain and gives a coastal pause enough time to become the center of the walk. The other loop can remain a separate reason to return.
Fun facts
- Route 24 follows the ridge described as the Devil’s Back.
- The western route approaches Long Cove; the eastern route approaches Gun Point Cove.
- Both sides are owned and managed by the Town of Harpswell.
Before you go
- Choose one or both loops and include the road crossing in the plan.
- Allow for rough footing and the climb back from shore.
- Use binoculars and keep distance from resting wildlife.
- Follow the town’s current dog and day-use rules.
Visitor perspectives
- Rebecca Goldfine enjoys the coastal views and seal-watching opportunities, noting steep shore approaches and occasional rough footing.
Capture
- Frame the cove through trees from a stable established route.
- Use a longer lens for distant wildlife without approaching resting places.
Social
Devil’s Back offers two coastal woodland loops on Orr’s Island.
Route 24 runs along the ridge between them.
Choose Long Cove on the west or Gun Point Cove on the east.
The western route includes mixed woods and old apple trees.
The eastern outlook offers a chance to observe rocky coastal habitat.
Rebecca Goldfine notes both rewarding views and occasional steep, rough sections.
Wildlife observation works best at a distance, without an expected sighting.
One loop today can leave the other as a reason to return.
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