QUICK TRAIL FACTS
- Preserve Size: Not sure
- Trail Mileage: 1.3 miles to second overlook
- Pets: yes
- Difficulty: easy to moderate
- Sights: remote ponds, views
These trails near Saddleback Mountain weave through mossy forests, with side trails to remote ponds nestled below the mountain and two overlooks. While you ascend a bit, it is not difficult hiking; the elevation gained is about 320 feet from the trailhead to the second overlook. It’s about 0.5 miles from the trailhead to Rock Pond, the first pond you reach, and just under a mile from there to the overlooks of Midway Pond and of Rangeley Lake. The trails can be a bit wet, especially at the start.
The main path is part of the Fly Rod Crosby Trail, and is marked and easy to follow. It intersects, eventually, with a multi-use trail that goes in one direction to meet up with the Appalachian Trail up Saddleback Mountain and beyond. The other direction takes you to the Cascade Stream Gorge trail.
I didn’t see any blazes on the trails to the ponds and views, but they are well-worn and easy to follow. The first view point looks out over Midway Pond and is pretty; from the other, I believe you can see as far as Rangeley Lake but the views were somewhat obscured by fog by the time we reached this point.
From the trailhead, my GPS says it’s about 1.3 miles to the second overlook, and about 1.8 miles to the intersection with the multi-use thoroughfare of the Fly Rod Crosby Trail.
Directions: You can pick up the trail at the end of Rock Pond Road — part of the Saddleback Mountain Ski Resort — where there is a small open area to the side of the road that looks suitable for parking. If it’s full, you can park in the first lot at the lodge and hike up to the end of Rock Pond Road.





