Day two of Travel Con. Second day in Portland. I had every intention of covering the conference in detail and haven’t really. The seminars are good and I’m absorbing things about YouTube strategy and blogging and audience building that I’ll put to use eventually. But what I keep finding myself wanting to do is drive.
So I let ChatGPT plan a lunchtime route.
I told it exactly how I felt about the city and gave it an hour and a half to work with. What it did — and I say this as a compliment — was take me to the parts of Portland that the downtown experience had not. The Pearl District first, which is cleaner and more navigated and has a restaurant row that reminded me of the outdoor dining setups that appeared in New York during the pandemic. Then up toward Washington Park and eventually Pittock Mansion, which I was less interested in as a mansion than as a viewpoint.
In this second day here in Portland, I continue my quest to find beauty in the city of Portland. I am starting to warm up to this place …
The City From the Hill
Pittock Mansion sits up in the West Hills with hiking trails running down from the parking lot and views of the city and Mount Hood beyond it. I parked, noted the signs about not leaving valuables in the car, and walked to the viewpoint. It’s the right kind of Portland to see on a clear afternoon — the skyline, the bridges, the mountains behind it. The city laid out in a way that makes you understand what it was before whatever it became.
Standing there I realized I’d been judging Portland entirely by downtown, which is an unfair sample. The neighborhoods outside the core are different. The Pearl District is different. The hills are genuinely beautiful. This is worth saying.
Then I walked back to the car and noticed I was standing in broken glass. Someone’s car window. Right there in the Pittock Mansion parking lot, surrounded by those helpful signs.
I don’t have a punchline for that.
Three Conversations
I talked to a security guard at the convention center. He said if I wanted to know what to avoid, his short answer was Portland. Then he said he thought the city was on its way to turning around, and that he was looking forward to it. That distinction matters.
I talked to a bartender at an Italian restaurant. She grew up here. She’s thinking about moving to Alaska. She’s a mother. Real estate is out of control and the city she’s known all her life isn’t the city she’s living in now. She wasn’t angry. She was heartbroken.
I talked to a woman working the cash register at one of the convention center food stands. I asked her for her honest opinion of what’s going on in her city. She opened up for a few minutes, trying to stay positive about where things were heading. When I said goodbye she thanked me for asking. She used to ride twelve miles each way on her bicycle to work. Since COVID changed things in the city, she doesn’t feel safe doing that anymore.
That last one stayed with me the whole afternoon.
On Being Honest
I’m at a conference where the sessions are covering travel bureau partnerships and brand sponsorships and getting paid by destinations to create content about them. I would love to monetize this someday. But I’m not going to tell you Portland is fine when three people who live and work here have told me something different. I’m not going to be that guy.
I’ve backpacked Europe eight or ten times. I’ve been to Asia, South America, all over this country. I can call things what they are. Portland is a city with real natural beauty, real good neighborhoods, real residents who love it and are grieving what’s happened to it. It is also, right now, a city that requires a certain vigilance I don’t need in most places I go.
I hope it finds its way back. I mean that. But I’m not going to pretend I found it.
On to more conference sessions. Then small towns. That’s what I’m built for.
And more about the conference over here! www.travelcon.org
