Urban hiking is about finding opportunity anywhere. Even if I don't know a place well, I try to get the lay of the land on foot. It's often much more interesting and rewarding than exploring by car. An example of this was that I was recently in Portland for Chris Guillebeau's World Domination Summit . The night before the conference, my cousin, a Portland native, invited me over for dinner. I hadn't rented a car, so I started thinking of ways I could get to his place. I turned to Google Maps and realized his house was located fewer than 5 miles away from my hotel downtown. When I looked at potential hiking routes to my cousin's home, I saw there were 3 parks on the way. My decision was made - I was going to urban hike to dinner! This ended up being a great experience. I hiked through Duniway Park , Marquam Nature Park , and Council Crest Park , which I learned is one of the highest points in the entire city. Council Crest was definitely the highlight...