Up, Down, and Why: Portland’s Hidden Staircases

If you have ever climbed a Portland stairway and suspected it was a cruel joke that went too far, you are ready for this walk.

Portland has a long, complicated relationship with stairs.

Not the polite kind. These are stairways that plunge into greenery, disappear behind houses, and reappear in places that make you question your sense of direction. They exist because Portland once ran on streetcars and the firm belief that walking uphill was character building.

On this walk, we will repeatedly abandon sensible streets in favor of concrete shortcuts that feel more like rumors than infrastructure. Elevation changes will happen abruptly.

The stairways will do what they do best - reveal things. Unexpected views. Ingeniously weird paths. Houses perched in places that feel optimistic at best.

Somewhere along our stair powered journey, we will encounter a giant sequoia that looks like it accidentally wandered out of a national park and decided to stay. It is enormous, completely out of scale, and impossible not to hug. Photos will happen.

We will start in Portland Heights, drop down through the Park Blocks, and finish in Goose Hollow. Yes, there is a restroom stop halfway through. We may enjoy stairs, but we are not monsters.

This is not a speed walk. It is a curiosity walk. Expect lots of stairs, frequent stopping, enthusiastic pointing, and repeated disbelief that this much weirdness has been hiding in plain sight.