Tailwinds to Oregon: The Carry-On Miracle
It’s time to hit the road again—or rather, hit the pedals. This time Chad and I are off to Oregon for a Backroads bike trip.
Now, packing for these trips is always its own saga. I’ve become the kind of person who makes a chart: every day we’re gone gets an outfit, and I don’t pack anything not on the chart. Theoretically this system helps me see which pants can be re-worn. (The pants don’t get a vote.) Still, despite my neat little chart, I have never managed to get it all into one small bag. A weeklong trip like this? Surely it was going to be the big suitcase. Chad even hauled it down for me.
But as I eyed the piles on the bed, I realized—maybe, just maybe—I could do this in two carry-ons. When Chad came home, I lit up like a kid at Christmas: “I have a surprise. Want to guess?” He deadpanned, “You’re pregnant.” I said, “Close. I’m in a carry-on.” He shook his head and said, “That’s just as much of a miracle.”
We flew into Portland on an evening flight, grabbed a rental car, and went straight to bed. Exploring could wait—though not for long. Thanks to our Eastern Standard body clocks, we were wide awake by 5 a.m.
Portland, at that hour, wasn’t exactly bustling. After some aimless driving, we cruised past Powell’s—the legendary city-block bookstore. The shelves gleamed at me through the glass, but with my new vow of “carry-on living,” I was actually relieved it wasn’t open. No temptation because there is no space.
The city itself felt exactly how I imagined Oregon would: giant fir trees, fog rolling over hills, mysterious in that “did I just walk into a moody indie film?” kind of way.
Breakfast finally materialized at Mémoire Cà Phê, a tiny Vietnamese brunch spot. My coconut milk eggs were divine, and of course we had to “share” a cinnamon roll (meaning I got my fair share and then defended it).
Fueled up, we drove west toward Mount Hood. Slowly, the fog lifted and the mountain revealed itself. Trillium Lake was postcard perfection—Mount Hood reflected in still water, kayaks sliding across, fishermen at the edges. There’s a flat two-mile loop around the lake, mostly on new boardwalks. Pro tip: walk it counterclockwise so Mount Hood is always in your view.
After that, we visited Timberline Lodge—built during the Depression as part of a work program, now buzzing with mountain bikers instead of skiers.
From there, it was a two-hour drive to Bend. Somewhere along the way, Oregon swapped costumes: the thick pine forest thinned, the ground turned golden, and suddenly it was desert. Not what we expected, but stunning all the same. Naturally, our next stop was the High Desert Museum.
The place is half museum, half zoo, and wholly charming. Statues of deer mid-duel greet you out front. Inside, Vicki the guide cheerfully told us, “Don’t miss the birds of prey! And at 3:30, we bring out the mammal.” My brain immediately leapt to: they’re going to feed a rabbit to the hawks in front of us. So with a puzzled look I asked, “to eat?” Poor Vicki nearly fainted when I asked. “Oh no, no! We’re bringing out a porcupine. We just… call it ‘the mammal.’” Note to the High Desert Museum: maybe tighten up that script.
The rest of the museum was wonderfully done, though I confirmed that I’d never have survived as an 1800s settler. Too many layers of wool, not enough wine.
Bonus points to the museum: they even have kennels where you can park your dog while you tour. Smart move—porcupines don’t need the added stress of a Labrador gawking at them.
We wrapped up the day in downtown Bend, which is about as hipster-meets-outdoorsy as you’d expect. Dinner at Zydeco Kitchen & Cocktails was excellent. The heirloom tomato salad and the beets salad are not to be missed.
After a full day of carry-on miracles, cinnamon rolls, porcupine misunderstandings, and changing landscapes, we tucked into bed. Tomorrow, the bikes take over.