Portland, Oregon Travel Guide: Bookstores, Bowls & Rainy-Day Coffee

Portland skipped the sun that week — Mt. Hood showed up anyway.

Portland was cloudy the entire time we were there, and it didn’t matter even slightly.

Portland, Oregon is a drive-to-the-parks, duck-into-bookstores, linger-over-breakfast kind of city — and if you calibrate to that instead of fighting it, a grey week here beats a sunny week most places. We came through on our Oregon road trip (after Ashland, which gets its own guide), saw friends, ate extremely well, and hosted a meetup. Here’s the playbook.

(And yes: I once wrote a guide to working remotely in Portland, Maine. Different Portland, same enthusiasm. The Portlands remain undefeated.)

Where to Stay in Portland

We stayed at this family-run Airbnb guesthouse — a private guest house tucked behind an artist’s property — and we book it every time we’re in town. Highly, highly recommend: it’s in a great walking neighborhood with cafes and shops close by, and it has that rare Airbnb quality of feeling like someone’s actual taste instead of a rental template.

What to Do in Portland

• Powell’s City of Books — non-negotiable. Budget more time and suitcase space than seems reasonable; you’ll use both. (Google Maps)
• Drive the parks and viewpoints — on a cloudy week the parks still deliver, and when Mt. Hood decides to appear above the treeline it feels like a personal favor.
• Walk your neighborhood’s shop street — ours had a stretch of great little shops near the café where we worked (more on that below).

Where to Eat and Drink in Portland

• cafe olli — our farm-to-table breakfast spot two mornings running, home of the best shaken espresso either of us has met. Full cafe olli review here. (Google Maps)
• The Whole Bowl — a vegetarian bowl so good it justifies a detour, and so confident it’s basically the entire menu. Full review here. (Google Maps)
• Case Study Coffee — moody, vibey, exactly right on a rainy day; we hosted our Make Writing Your Job subscriber meetup here. Full review here. (Google Maps)
• Also on our receipts: Eem (the Thai barbecue everyone tells you about — they’re not wrong to) and a rotation of bakeries that kept the cloudy mornings civilized.

The Verdict on Portland

Three or four days is right: one for Powell’s and downtown, one for parks and viewpoints, and at least one with no plan beyond breakfast and whichever café adopts you. Cloud cover, as it turns out, is just good lighting for bookstores.

For the southern half of this road trip, here’s my Ashland, Oregon travel guide — and the full travel archive if you’re planning bigger.

This is part of my travel series — I spent five years reviewing places around the world as a digital nomad (all the guides live here), and now I road-trip out from San Francisco with the same notebook. Subscribe to my newsletter for new guides and reviews — and if you’re a writer who wants a career that travels this well, that’s what Make Writing Your Job is for.