This lollipop loop can be done from either the High Point trailhead or from SE Preston Way. The SE Preston Way trailhead can be easy to miss, but it's not a busy location, as most hikers use the High Point trailhead. (A Discover Pass is required at the High Point trailhead.) The loop links together the Preston Powerline, Lingering, Tiger Mountain, West Tiger RR Grade, and Preston trails together.
Along this gem of a trail are lots of big leaf maple, ferns galore, wild ginger, huckleberry, mountain ash, clasp leaf-twisted stalk, salmon berry, devil’s club, ghost pipe and big snails — potentially unlike you've ever seen before. There is wildlife in the area, including black bears. In the right season, you'll be sure to find daisies, butterfly bush, hedge nettle, bird’s-foot trefoil, hawkweed, ocean spray, foxglove, ajuga and wild berries.
Starting from the SE Preston Way trailhead, look for the sign about 25 feet away from the road, up a very short uphill bank. The trailhead begins at the end of a cyclone fence of a private residence on the left. A Department of Transportation facility is within sight on the right. The trailhead sign is definitely weather-worn.
Hike 500 feet past the trailhead sign to connect with the rocky powerline road, completely exposed, but with an explosion of wildflowers along the way. Head to the right for counterclockwise loop. The loop begins 1.4 miles in by going left at Lingering Trail sign. The meadow area here is a bit overgrown, but you can see the turnstile ahead that leads into the forest.
At 2 miles, find a trail sign for Dwight’s Way, High Point Trail and Preston Trail; continue on Lingering Trail. At 2.39 miles is a junction, follow the sign to Tiger Mountain to the left. At 3.45 miles, continue left to Tiger Mountain. At 3.73 miles, go left at the junction to continue the Preston Loop Trail. This location is at 2,100 feet elevation with mountain views. The descent begins here.
At 4.69 miles, continue straight ahead for the loop; however, there’s a trail sign at this cross junction, for Bootleg Trail to the right. In about 400 feet, an unmarked trail on the right continues the loop — keep an eye out, as it is easy to miss.
The trail descends quickly through overgrown and rocky terrain, so it’s a bit slow-going. At 5.55 miles, stay on the lower trail. At 5.90 miles, take a break and enjoy stump man! Be sure to go left after greeting him to continue the loop.
At 6.04 miles, go right at the junction with the sign for Preston Trail. After a handful of switchbacks, eventually the trail comes back to the rocky powerline trail, passing by several private residences along the right side. Watch for the opening into the forest on the left for the trail back to the trailhead.
WTA Pro Tip: There are many options for exploring other trails to add mileage with generally good signage, but a good trail map, as well as a satellite tracker, are great for route finding when signage is lacking. The area is truly beautiful for a hike or trail run.



