Celebrated for “coolness” and non-conformity, this city may be the biggest in all of Oregon, but its laid back vibe, walkability and access to the great outdoors make it feel more like a big town. Locals love to be outside which is why the city has detailed urban trails mapped out. Try the Alameda Ridge and Stairs route. Visit the renowned Japanese Garden and the Lone Fir Cemetery in the fall for colorful leaf shows.