Day three of Travel Con. Last full day in Portland. I decided to give the city one more chance to show me something worth remembering, and I let ChatGPT plan the itinerary.
I gave it my parameters — 24 hours, starting now, give me a positive impression before I leave — and it sent me to the International Rose Test Garden, Pittock Mansion again, a waterfront area along the Willamette, and the Pearl District for dinner. Four stops. I did three of them properly and scouted the fourth.
The Rose Garden
I was there off-season. The blooms won’t happen for a while yet and I knew that, but some flowering trees were doing something in the morning light and the grounds themselves are worth the visit regardless. I’ll come back in bloom season if I’m ever in Portland again in the right month.
Pittock Mansion, Properly This Time
I went inside. The mansion itself was built in 1914 by Henry Pittock, who ran The Oregonian for decades, and the interior tells that story — formal, well-appointed, the kind of house built by someone who understood what lasting looked like. But I’ll be honest: I went for the view. Coming down from the grounds into the West Hills neighborhoods below, the city opened up on one side and the natural landscape on the other. The scenic drive back down reminded me why I keep taking the roads that look like they might not be worth it. They usually are.
The Willamette Waterfront
This is what I’d been looking for. There’s an area along the river — I want to say near the Willamette, the flowers there were gorgeous and the harbor visible behind them — that felt completely different from anything I’d experienced in downtown Portland. Cafes with tables outside, a restaurant row, easy parking, the kind of neighborhood that felt genuinely inhabited rather than survived through. Someone mentioned it felt European and they weren’t wrong. It had a Zurich quality to it, or maybe Stockholm. Water, flowers, a reasonable sense that people were choosing to be there.
I had a late breakfast at a small café and sat with it for a while. Every city has its cool places and its places to avoid. That’s what I keep coming back to. Portland’s cool places are genuinely cool. The problem is navigating between them.
The Tent City I Didn’t Film
I scouted the waterfront area near the convention center as a possible night photography location — wanted to get the skyline with the water. What I found was a large encampment. More tents than I’d seen anywhere, plus a few long-term RVs, a community of people living outside in a city that can’t figure out what to do about it.
I want to be clear that I’m not judging the people who are there. What I find myself genuinely curious about is the why and the how — what the chain of events looks like that leads someone to that place, what they need, what would actually help. That’s a documentary. Not one I can make by wandering in alone with a camera. You’d need a fixer, a local guide, someone with real relationships in that community. I don’t have that. So I drove past.
Denise sent me pictures from back home that evening. There’s a cat that lives outside near her office — homeless, surviving on whatever she leaves out for it. She’d found where it sleeps. A bed of leaves in a ditch. I sat in my hotel room in a comfortable chair in a comfortable hotel and looked at those pictures for a while.
I don’t have any answers. I’m just one person driving around the country pointing a camera at things. What I can do is try not to look away.
Dinner at the Mediterranean Exploration Company
The Pearl District for dinner, as ChatGPT suggested. Hummus, octopus, lamb kebab, a naked Negroni without the alcohol, an alcohol-free Italian beer. If you told me six months ago I’d be three months into not drinking and not missing it, I’d have been skeptical. Here I am. The food was excellent. The neighborhood felt safe. If I ever come back to Portland I know where I’d stay.
Tomorrow: mystery location. We’ll talk about it in the morning.
