By far the best feature of the park is the variety of routes that can be taken through it. Two hour runs are possible, as well as quick 30 minute out and backs. As a whole the park is incredibly hilly, so be prepared for runs that are a bit harder. Another thing to watch out for is the mud. The park lacks decent drainage in a lot of spots, so be prepared to splash through some sections. If you do get a little dirty and don't want to hop right back into the car, the Lewis and Clark Law School borders the northern end of the park, and has shower rooms that are usually open during the day. They are located in the Gantenbein student center (campus map here).
My only complaint with the park, and this is rather easily rectified, is that it is confusing to learn how to navigate through it. Initially, trails with seem to end and begin at random, and will pop you out into some random neighborhoods. However, once you run through it a couple of times, or accompany someone who knows the park, you'll find that it begins to make sense.
Directions: From downtown Portland, take I-5 South and take exit 297 for Terwilliger Blvd. Bear right off of the exit onto Barbur Blvd and take the first right onto Terwilliger Blvd. heading South. Continue on Terwilliger Blvd until you hit the traffic circle. Take the second exit off of the circle (the Law School is the first exit) and continue down Terwilliger for about another mile. The parking lot for the park is on the right.
Website with trail maps: http://www.tryonfriends.org/
Below are trail maps of the Upper, Middle and Lower sections of the park.
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