Oregon City, Oregon is the oldest city west of the Mississippi and the destination of pioneers on the Oregon Trail. As expected there are lots of historical sites around the small town of approximately 30,000, but one of the things that stand out to me is the number of scenic outlooks. Built on a bluff that overlooks rivers, the distant Portland metropolis, and even more distant Cascade mountains there is plenty to soak in. The best time for this is fall season when everything is in festive colors and the air is crisp. If in the Portland area take the afternoon to drive down and check out this interesting old town.