This ride is nearly an all off-pavement tour of the ecosystems on the leeward side of Wy'East. It is over 90% off pavement and includes a mix of graded gravel, rutted double-track and single track. In mid-May the upper single-track was still filled with winter fall down, so the travel time on the loop can be quite prolonged earlier in the year. It really consists of two loops combined into one longer ride. The first and lower loop is around the Jordan & Tygh Creek watersheds though the White River Wildlife area and Mt. Hood National Forest. The second & upper loop is a though Mt. Hood National Forest dropping down upper Fifteen Mile Creek. Starting in Friend, Oregon at Friend School is a nice parking area and two primitive outhouses. Step inside for a bit of time travel. Heading south you immediately drop into the White River wildlife area (Closed December 1st - March 31st). I rode in June with the most recent rain about a week earlier, so the ground was tacky. The initial smooth road rapidly deteriorates into rutted and chunky double track. Oaks and dry grass lead into Jordan Creek where a bit of green hugs the banks of the stream. As the stream drops into a canyon, you ride along a bluff with a few overlooks into the canyon. At Shadybrook road, you could head left into Tygh Valley, but straight ahead is a Dead End sign, to be ignored on a bike and you cut back uphill on McCorkle Grade road. Back up on the plateau, there appears to be a gate, but just beyond there is no fence and you can continue on the again rutted double track. It is more dirt than gravel and occasionally sand. After touching NFDR 27 momentarily, you follow the margin of the wildlife area on road 2700. You join North South Road for a winding, rolling route along the contours. This area is gated off from all motorized vehicles. The stream bed of Tygh Creek is an ankle-deep ford and there are numerous large logs across the road. The creek is shallow and wadeable, but I couldn't ride though the rounded boulders in the stream. North facing slopes are coniferous and south facing slopes dry oak scrub. The second loop begins at Friend road, later Cold Springs road, a smooth and wide, mostly gravel ascent into the cooler air. There are two roadside rock outcroppings, great for lunch, looking south over Jordan Creek valley near the top of the climb. Shortly after crossing Fret Creek, Fifteen mile campground is on the right and marks the beginning of a 3 hour descent. There is a modern outhouse at the campground. You can just as easily take Cedar Creek trail from here. However, Fifteen Mile Trail #456 is a bit more flowy, at least once the winter fall down is cleaned up. There are several meadows to stop in and admire the valley. You are somewhat likely to encounter other mountain bikes riding this section of 44 trails. The intersection with Cedar Creek trail again is the end of the first section. The next section tends to be less used and much more overgrown with shrubs. It initially follows near the creek under the conifers and the lower portion runs a little higher along the south facing slope in the dry Oak scrubland. There are two wooden bridges that are descending into rotted disrepair with a few boards caved in and the support beneath the bridge somewhat in question. They still seem relatively useable in 2020. At the end of the trail, meeting with NFDR 4421, do not go right as all my maps (based on Open Street Map) suggest. Turn left, uphill for less than 50 meters and take the chunky trail/road dropping to the right. This drops you quickly down onto the intersection of Fifteen Mile creek and NFDR 4421 (or North South road as some of my maps read. It is a moderately steep 2 km climb to Shell Rock road, which drops as a rutted double track. It then levels out into a gentle descent that is dirt. You can surf back and forth over the center hump for play. It is a very straight shot to Heberlein Road. Passing each ranch, the road becomes flatter, wider and more graded gravel. Heading south on Heberlein, there are views back toward Lookout Mountain that you just descended for 2 1/2 hours.