I've travelled all over the world. The first thing I do in a location is take a nice tour then spend the rest of my time exploring by myself and going to events. For our trip to Portland, I wasn't sure how much we'd get out of a general tour. Decided to look at trip advisor and see if there were any interesting tours and there was... Forktown Tours.
From the first call they were great. All booked up but would see what they could do. They found us a guide that had just returned the night before from Italy. Even though it was just two of us and they don't do tours that small, they made an exception. Our guide pushed through her jetlag and gave us an amazing tour. We got the history of the city over delicious little meals up and down Mississippi Ave. It was the perfect alternate to a general tour.
Our guide/co-owner was knowledgable, sweet, and accommodating and the employees and managers of the restaurants we visited were charming and gracious.
The Forktown tour is a must.
*One warning. Do not eat before because you'll want the room for every bite offered.