The Wildwood Trail is thirty miles long, accessible from a dozen trailheads, and runs through what is allegedly the largest urban forest in the country. The trick is picking the segment that gives you the deep-forest feeling without the trail itself becoming the experience.
The default Forest Park hike (Lower Macleay to Pittock Mansion via the Audubon trail) is fine. It’s also crowded on weekends and ends at a tourist mansion. We recommend a different segment: Cumberland Road trailhead to Wildwood Trail, north to the German Hill junction, and back. About 5.5 miles round trip with 800 feet of gain; the kind of hike that’s long enough to feel like a hike and short enough to do after lunch.
Cumberland Road is on the west edge of the city — you reach it by driving up Burnside Road and turning right on Cumberland. Tiny gravel lot, maybe six cars, never full on weekdays. The trail descends 200 feet to the actual Wildwood path and then climbs slowly along the ridge. Western red cedar, Douglas fir, sword fern at knee height in late spring.
The German Hill junction is where the trail crests; there’s no view there but the silence is the point. Most weekends you’ll see maybe four other hikers. Compare with Lower Macleay (200 hikers per hour on a sunny Saturday). Same forest; different experience.
Bring water. The trail is shaded for most of the route but there’s no creek crossing on this segment.