I had my first century (100-mile) bike ride from Portland to the Oregon Coast. The plan was to take the Max with the bike to Hillsboro, then ride along the Banks-Vernonia trail, then Hwy 47 to Hwy 202 from Vernonia, to Mist, then Jewell, Olney, then up to Astoria and back down to Seaside where we were staying for the Memorial Day weekend.
Of course, things did not go according to plan. I got a flat on the first mile! Had to change the flat in the pouring rain, then got lost due to a new subdivision that went in and was not on my map. Once we got out of Hillsboro and over to Banks things started to get better. We followed the directions to the head of the Banks-Vernonia trail, which is a nice 30-mile paved path off the road. It was an old abandoned railroad path.
So the ride was great until you got closer to Vernonia. The Vernonia flood of 2007 had washed out part of the trail and the road bike rider turned into a cyclocross mountain bike ride. It was a total mess and the that leg of the trip took almost 4 hours.

By the time we got to Vernonia we knew there wouldn't be enough daylight to make it to Seaside. But we continued on, Hwy 47 and Hwy 202 was an incredible segment of the ride, with very few cars and beautiful scenery. We were chased by a few dogs that seemed trained to attack bike riders, but we had enough energy to outpace them.