Oregon April 2026

Oregon had lived in my mind long before I ever stepped foot there. Maybe because the childhood show Gravity Falls was inspired by it. Or maybe because of those photos of Haystack Rock that always seemed too beautiful to be real. Either way, this April I finally made my way there alone though lately, many of my trips seem to unfold that way.

I started in downtown Portland, and if I’m being honest, I wasn’t immediately charmed. Then again, perhaps I arrived with the wrong lens. As much as the city girl in me dreams of a quieter, slower life someday, I’m still coming from Chicago. My idea of “downtown” is hard to shake, though truthfully I don’t always favor it there either.

Still, I settled in. Everyone wore flannels. I considered buying one myself but decided not to commit that fully to the experience. Instead, I grabbed coffee from the hotel across the street, wandered through Powell’s City of Books, added far too many books to my suitcase, picked up Thai food nearby, and called it a night. Strangely enough, it all felt familiar the kind of quiet evening I’d probably spend at home anyway.

The next morning I drove out to Silver Falls State Park where I spent the day hiking past waterfall after waterfall, each somehow more beautiful than the last. I’d be lying if I said I wasn’t nervous at times. There’s something unsettling about realizing you’re alone in the middle of the woods, even when there’s no real danger at all. But every so often smiling strangers would pass by, and around me were the trees, birdsong, rushing water, the comfort of nature itself. So perhaps I was never really alone.

The rest of my trip was spent in Depoe Bay, which completely stole my heart. If I’m allowed favorites, that little coastal town was certainly mine. The drive there alone felt cinematic. I still can’t believe I’m old enough to rent a car without it feeling slightly absurd.

But Depoe Bay felt like stepping into a coming of age film. Saltwater taffy shops, whale watching signs, clam chowder by the water, overly sweet wine that leaves you with a headache, the kind of place that makes you nostalgic for something while you’re still living it.

I even developed a slight crush on the guy running the whale watching tour, mostly because he helped me put my life vest on. Which, to be fair, he didn’t help anyone else with, so naturally I chose to read into it far more than I probably should have.

Nonetheless, I’m back in Chicago now, already wondering where I’ll wander off to next.