If you are outside of the central Portland area you might be surprised that it's easier than you think to get to downtown Portland for an evening. Just take the Max Light Rail. The Light Rail is my choice to avoid the hassles of the one-way streets, parking fees, pedestrians and bicyclists.
I recommend getting off Max in the center of it all... Pioneer Courthouse Square. You'll be close to Pioneer Place for shopping and casual dining as well as the department stores that face the square. Area Map.
For an interesting walk, walk 5 blocks along the Park Blocks (SW Park Street) to the Portland Art Museum. The museum is open until 8 p.m. on Thursdays and Fridays. You can enter the museum between SW Park and SW 10th.
As you walk, you'll see historic churches, museums and get a sense of the downtown Portland lifestyle.
Hungry? There are some wonderful restaurants in this area. My choice for a cozy, yet elegant meal, is Raven and Rose at 1331 SW Broadway. Located in the historic Ladd Estate Carriage House, the restaurant is reminiscent of an upscale pub. While the pool table is upstairs, the main dining room downstairs offers diners a creative, top notch food and beverage menu. Happy Hour is offered upstairs in the Rookery. Reservations are recommended for dining.
For another option, keep walking on Broadway to Higgins at 1239 SW Broadway. While they are known for delightful desserts, their tables, covered with crisp white linens, and locally sourced menus beckon the downtown walker for a lunch or dinner.
As you continue back down Broadway toward Pioneer Courthouse Square, you will enjoy the bright lights of the Arlene Schnitzer Concert Hall and downtown buildings.
Walking is best done in the early evening for sightseeing. If you are headed for a concert or downtown event, check the Max Light Rail Schedule for your return to minimize your wait at the light rail stop.