This hike through Washington Park is a flexible 7.6-mile roundtrip (you can turn around when you've had your fill). The park will make you feel like you're escaping the city without ever leaving. If you're interested in mountain biking, there are trails available.
Take the train to Washington Park and hike through Hoyt Arboretum. This will bypass a few miles of Wildwood Trail, but you won't miss much.
In the arboretum, the trail twists and turns through the trees, will smaller trails jutting off to the sides, through other groups of trees (each trail is aptly named for the type of respective tree). Continue on Wildwood and eventually, you will cross Burnside Street, then climb gradually to Pittock Mansion, where there is a great view of the city, as well as toilets.
Past the mansion, you will start to descend – at the bottom, stray left off of Wildwood to take a shorter route to Cornell Road. Cross the street, where you will see a picnic area and parking lot. The trail descends again, and soon you will come to an old stone structure, where the trail splits – one heads out of the woods into a neighborhood, and the other continues into the park. You can either turn around here for a 7.6-mile hike roundtrip or continue on for as long as you choose – Wildwood Trail runs 30 miles long point-to-point.