When planning routes for my urban walks, I have standards: the route can't be found elsewhere; must be a loop; must have a story to tell; must contain somewhere to spend money, whether on coffee, beer, or books; and must be at least three miles long, preferably longer.
When I begin planning, my first thrill comes via topographic maps: tight contour lines mean views. Great views are one of life's sweetest rewards. Then, before I research the area's natural or cultural history, I'll map out a route, using what I already know about it. Next is research into the area's National Historic Districts, if any, and mining of the text (and bibliographies) of old Portland books, for offbeat sources of information. Then I drive/walk my draft route, making changes as I encounter a wall made of nineteenth century ballast stone, a park where two streams converge, or a lonely bridge spanning an isolated forest canyon.
My goal is to have each neighborhood, park, and the city's geologically varied landforms tell their stories so that a walker can see why they're here, who and what created them, and discover dozens of reasons to come back to enjoy them again. Here's a list of things that make for a great urban trek:
1. City staircases, at least fifty, preferably in one staircase. The steeper the better.
2. Alleys, unpaved, ideally, with old apple trees and unimpeded views of backyards.
3. Dead-ends with unmarked public right of ways behind them that let you shortcut the street grid and go where the neighbors would rather you not.
4. Free-flowing creeks in the heart of the city.
5. Walls, tunnels, buildings, anything built by the WPA.
6. Old Carnegie libraries.
7. Old school buildings with their quaint touches: a sundial in a gable end; a terra cotta girl, pigtails hanging down, over the girl's entrance; an old "keep off the grass" sign embedded in the wall, evidence of an era when adults were sterner to children.
8. Odd vantage points, like under the soaring, surprisingly beautiful arches of a freeway bridge, or inside the world's longest enclosed pedestrian bridge.
9. Trees or bushes with an interesting ethnobotanical pedigree.
10. An assortment of man-made quirks: a yard filled with rock cairns, a home that has turned its chimney into a rock-climbing wall, a wall embedded with hand carved stonework recycled from a demolished downtown office building, a street of houseboats long ago hauled up the bank and turned into regular homes, but with subtle clues to their past, if you know where to look.
11. Districts on the National Historic Register: they always have a story to tell.
12. Architect-designed homes, or neighborhoods of kit bungalows and foursquares ? always charming, and in Portland, invariably lovingly restored.
13. Big trees that haven't been topped.
14. Landforms created or impacted by the Missoula Floods.
15. Cemeteries and Water Bureau property, de facto parks that don't get much attention from the general public, and which invariably offer views and peace.
16. Transitions: where industry meets residential, cliff meets bottomland, neighborhood segues into forest, river meets its beach, or forests canyons hide under freeway bridges, a green world unseen by the speeding vehicles flying far above.
17. Most important: a commercial district, preferably from the streetcar era, of local shops and restaurants, because every walk deserves a destination to anticipate.
The book I'm writing now, Portland City Walks, is like Portland Hill Walks, but it covers some classic neighborhoods too flat for the first book, such as Irvington and Piedmont, and five historic towns around Portland, such as Oregon City and Vancouver. My favorite comment when I give walking tours is from native Portlanders who'll say, "I never knew that!" There's a universe of intrigue and forgotten stories on every street.