Oregon Trail Tour 2026

"As I stared over my boots toward the hills, I realized that I had resolved for myself one of the great debates about the overland years. Some historians, often called "economic determinists", argue that America's frequent cycles of financial collapse and farm failures drove the majority of pioneers to the trail. Other scholars, "adventure theorists", postulate that romantic yearnings for exotic travel and for fulfilling manifest destiny were more dominant motives. Reaching middle Nebraska, I decided, had turned me into a diehard economic determinist. Forget adventure. Adventure gets pretty stale after a while and you're not much of a romantic after a month on the trail. No one would do this, day after day, unless he had to." Rinker Buck, "The Oregon Trail".

I wholeheartedly agree. Adventure is great fun for eight days. But four months, with the added bonus of life-threatening CALAMITY cards in the deck? It was because the emigrants felt they HAD to, not that they WANTED to.

I headed into my last day jazzed. My bike mechanic friend in Hood River had told me, "They've just finished the Mitchell Point Tunnel, the last phase of the reconnecting the old Columbia River Highway all the way to Portland! All you have do to is ride the first mile on the interstate, then take the cutoff, and enjoy the ride!" Wow, what a pleasure!

I did my interstate mile, took the cutoff, blew through the new bike only tunnel, but upon exiting hit a "Road Closed Ahead" sign?!? I took my usual approach of "Closed is for other people", continued, but hit a construction crew in a half mile: "we are still building this section of the trail, this is closed for a couple of miles". Ugh - backtrack the two miles back to the interstate, repeat those miles and a few more on the interstate until reaching the exit beyond. But it was early, traffic was light, #OregonTrail - could be worse. And having reconnected with the trail, I finally got my picture and VIDEO of a deer!

I rolled into Cascade Locks, the only thing resembling a town in the fifty miles between Hood River and the Portland suburbs, to refill water and get some road food. The teenager behind the counter in the convenience store was curious - he clearly thought what I was doing was the coolest thing :) He's born and raised in the Gorge: "It's the best place in the world". Hard for me to argue with that.

I rolled out of Cascade Locks and immediately ran into another sign: "Trail Closed Ahead Due to Landslide" - wow, how #OregonTrail is that! (I had learned at the museum the previous day that landslides are a constant feature of the Gorge. The surface basalt rock layer sits on a sub-surface of clay. Water seeps in, ultimately works its way down to the impervious clay layer, then it's like a Slip N Slide for the basalt, Voila Landslide). Mr. Google told me I needed another half-dozen miles back on the interstate to work past the landslide. Sigh, but OK.

Back again on the scenic road, I entered waterfall country: five significant waterfalls over a dozen or so miles, the big daddy being Multnomah Falls, over 600 feet high, the 2nd highest waterfall in the USA. I arrived at Multnomah with the sun directly behind the waterfall, so no photo of it, but I included a different waterfall photo as an example.

I knew I had one BIG climb to clear - 700 feet up to Vista House, the final awesome view of the trip, only fifteen miles from Portland. Thirty solid minutes of work - I was there, (Video) and it was literally downhill all the rest of the way. I stopped halfway down for a wonderful pulled pork sandwich at a local hole-in-the-wall, and then cruised on into Portland, fed and feeling great. You can see the smile in the "Welcome to Portland" photo! I even got the bonus of enjoying a dinner with a cousin who lives in Washington who I had not seen since I was a boy. My adventure was over. 580 miles, 24,000 feet of climbing - check. I even got a bonus send-off from the gate agent at the airport. As I was checking the massive bicycle bag, she asked where I had used it, was extremely impressed, told me that she had lost her sister to cancer last year, thanked me for what I was doing and shook my hand :)

My yoga instructor Rosie always encourages me to reflect on "what did you learn from this experience?" I read this morning my reflection from the original Virtual Transcon trip; all of those themes applied to this one. But beyond that, two key specific concepts emerged. First, the people I met along the way had a consistent tone: one of "minding their own business" - unlike most other trips (especially in my tours through southern states) where curious people asked where I was going and what I was doing, I got literally zero of that on this trip until the teenager on the final day. I think in the rural West, there is an implicit "your business is your business" approach. People engaged when I engaged them, but I had to initiate those conversations. This is neither bad nor good, but it is very different than my previous experiences.

Second, I realized - these people live their lives in a far more "present" way than I do, then most of us do. I'd go into a café and people were talking to each other, interacting with each other - because they know each other, they are family, friends, neighbors, their community. I usually roll my eyes at people walking down the street wearing headphones and staring at their screens - I was now the one looking down at a screen in public. Related, but slightly different - a notable absence of "outside big city stuff". Besides the one Seahawks transplant I noted, no sports team stickers or regalia. Including college teams - few of these people go to college (I checked: small towns like Vale where I stayed the first night, 10% college grads vs. over 40% nationally, larger towns like Baker City or Pendleton are in the 25% range.) These are people who grew up in their town, stayed there, have known the people in their town forever, and their lives and their personal relationships are centered there. I grew up in a farm town of 3,000 and I totally understand and respect that their lives and associations are in many ways more real and connected than they are for those of us living on a bigger stage.

I'll close on one more thought. Traveling the Oregon Trail was a team sport. In Missouri, pioneers formed groups of several dozen wagons. The community stuck together for safety and to help load and unload each other's wagons to maneuver up and down hills or across streams. You guys are my team. You are in my thoughts throughout the trip, your notes of encouragement keep me going, and obviously your financial support makes all of this meaningful. Lord willing, I will be back doing another Crazy Bike Adventure next year. I turn sixty-five in the fall, I know I'll reach a point where doing this won't be possible, but I'm pretty sure I have at least one more in me :) THANK YOU!