“People came west to get away from the government. Now they have no place else to go, so they think of new ways of doing things.”

That’s Bud Clark, the colorful ex-mayor of Portland, Oregon, talking to me recently over a Reuben sandwich at his tavern, the Goose Hollow Inn. When you go west, in the U.S., you don’t just wake up three hours behind the East Coast. You also play by different rules.

After trips by train in the Northeast and taking gravel roads across the mountains and prairies, I’m finishing off this year’s series of American road trips with two of my favorite states: California, where I once lived, and Oregon, my new home.

Portland may be known for Portlandia—and a certain wacky spirit—but not as many know what it looks like. I’ll ask locals about what image defines the city, and chart out a worthy bike route as I go.

Then I’ll check out a couple of Oregon surprises, both only a few hours from Portland’s food carts: a homestay with real-deal cowboys (and cowgirls) past the Cascades in central and eastern Oregon, and Corvallis, a university town that makes its own tailgate food and home to the Oregon State Beavers.

A decade ago, I lived in San Francisco, commuting across the Bay Bridge daily—but I never stopped at its pit stop, Treasure Island. This time I’m staying there to see what’s happening in a changing neighborhood. Then I’ll use the BART (Bay Area Rapid Transit) to explore valley towns and wineries often missed by Bay Area visitors.

It’s become hip of late to go mobile around here, with the off-site tech crowd renting or buying vintage trailers and hitting the road. I’m renting one and returning to Highway 1 and Big Sur. This is my first solo trailer experience. Anyone have any tips on backing up?