A train and two buses is all you need to spend the day at Timberline Lodge: take the MAX to Gresham, a bus to Sandy, and an hourlong $2 public shuttle to the mountain. Go in the morning, hike to Ramona Falls, and enjoy a trailside picnic or a stop at the Ram’s Head Bar. Miss the bus back? Get a room at the lodge and watch the sunset from the hot tub. 

A TriMet transfer is good on regular C-Tran routes to Vancouver. The no. 4 picks up at Delta Park and Jantzen Beach, and drops riders in the heart of downtown. Officers Row, the gorgeous main library, a walkable waterfront, brewpubs, greasy spoons, and Esther Short Park are within an easy stroll. Raining? Duck into the Kiggins Theatre, serving beer, wine, and, this summer, a series of nostalgic ’80s screenings. 

Take a quintessential two-wheeled day on the Springwater Corridor, now paved all 21 miles east to Boring (Boring!). With the Oaks Bottom Wildlife Refuge, the “Milwaukie Ballet” (a.k.a. the Acropolis strip club), the Cartlandia food cart pod, the Leach Botanical Garden, and Powell Butte Nature Park all just off the path, your adventure could spiral in any direction.