Begin at the base lodge of Saddleback Mountain starting out on the Wheeler Slope trail directly in front of the lodge, to the Gray Ghost trail, on to the Tri-Color trail. The path is fairly well-worn and marked by stakes. The Tri-Color trail will bring you to the top of the Kennebago Quad, where a short, narrow trail starts behind the upper building and leads to the Appalachian Trail and the summit of Saddleback Mountain. This is approximately a 2-mile route to the summit. Be sure to stop on your way up to take in the gorgeous views. For a more moderate explore on Saddleback Mountain, we suggest the Rock Pond Trail: The trailhead is located at the end of the Rock Pond Condos Drive and climbs gradually along a dirt and grass path. Be sure to explore for a bit before going back up to reach the trail to Midway Pond and the two scenic overlooks. This trail splits from the trail you have been walking on. They are marked but keep aware of your surroundings. The trail towards the overlooks climbs at a moderate rate before reaching the two viewpoints. Keep an eye out for the Midway Pond Trail, too. The trail terminates at the second overlook so you’ll be turning around to get back to the main trail. The trails are marked with some signs and white blazes but there’s a bit of “weaving and bobbing”, so keep aware of your surroundings.
Directions: From Route 4 near the Whip Willow Farm Overlook, take Dallas Hill Road, about 2.5 miles, you’ll turn right onto Saddleback Mountain Road. Follow this about 4.6 miles until you reach the Saddleback Ski Area with the base lodge on the left. Continue up to the parking lots, taking the first road on the left that leads up through the condos. Follow to the end and you’ll see a small parking area, a sign, and the path.