Oregon Trail Tour 2026

"On the top of this bluff, the road divides, one leading to the Columbia River. The other, at the left, is the one we took." - Riley Root, 1848

When the emigrants reached The Dalles (rhymes with 'vowels'), at the head of the Columbia Gorge, the Oregon Trail split. In the early years, there was one choice - load your wagon on a raft, float it down the river through rapids, and risk losing all your possessions and drowning given the swift, uneven current. But in 1846, an entrepreneur, Henry Barlow, offered a second choice: a toll road providing a twelve day slog up and around Mount Hood, and then down its backside into Oregon City. All the time hoping you didn't catch an early season snowstorm, or a landslide, or other Oregon Trail CALAMITY cards. Like Sophie in the movie, there are no good choices, just a choice that must be made.

For travelers who arrived late in the season, the mountain option was untenable, so the rapids were the only choice. And so it was for me. My original plan was to take the Barlow Road up to Mount Hood and then coast down to Portland. But my lost time due to several days of headwinds meant that like the late-arriving emigrants, my path would be straight down the Columbia - albeit on a modern road, not a raft.

My day began with a crossing to the Washington side of the river (video) to take in a unique structure pointed out to me by donor Ron: a full-size replica of Stonehenge, built to commemorate the World War I dead of Klickitat County, WA. It was a little surreal to be standing in the center, looking down at the Columbia and all around, in this epic structure, not a soul in sight. (video).

The twenty miles on the Washington side down to The Dalles were delightful - quiet roads, great scenery. Crossing back into Oregon at The Dalles, I enjoyed an awesome second breakfast and then toured the Columbia Gorge Discovery Center, which (naturally) had its Oregon Trail exhibit, focused on the choice of the gorge vs. the overland route (see tableau photo below). There was a voice track to the covered wagon / raft in the photo, let's just say they had had a harrowing experience and were hoping for a hot bath once they reached Portland :)

I left the Discovery Center with only twenty miles to cover before my overnight destination of Hood River. They ended up being the best twenty miles of the trip. The Columbia River Highway was finished in 1922, the first scenic highway in America. East of The Dalles, it was built over by I-84, but the rest of the way to Portland, you get to follow the quiet scenic route. There are climbs up 600 feet to an overlook at the top of the gorge (video). There is a tunnel, in a section that is "bike only", with no car worry. More climbing than the interstate, but every climb rewarded with a spectacular view. I rode up to the summit with some other cyclists who took a photo of me at the top. On the flats, I was singing "Proud Mary" - rollin' on the river!

I rolled into Hood River by 2pm, my earliest finish of the trip, and then played my final TOWN card. I had flatted (3rd of the trip) in the morning, so was down to one spare tube. I also had noticed yesterday that I had a slack spoke on my rear wheel - the "Broken Spoke" card. I found a local bike mechanic who was kind enough to fix my wheel and sell me a couple of fresh tubes. He, like many people, had relocated over the last decade to Hood River - a chill spot an hour east of Portland, with none of the baggage that Portland has accumulated. It's a new shop for him in a cool neighborhood in the "heights" of town, clearly upscale. If you're ever in Hood River and need a bike fixed, go to Dirty Finger!

Main drag is lined with upscale boutiques, nice restaurants and bars. Much nicer place than I expected, the laid-back "nice" vibe of Baker City, but more upscale without being flashy. I stayed in the old-school Hood River Hotel downtown, nice place, room just over $100. Big money hasn't arrived, but I'd be speculating on real estate here…

I'm a big believer that "things work out the way they were meant to". Even though I wasn't planning to take the Gorge, I am SO HAPPY that I did -- such a beautiful place and an awesome day!

PS -- I'm OK confessing this now, but the last two days in the previous post: between the wind, the hail, the interstate and the bike problems -- low points. Today was the best day of the trip, and with clear sailing on quiet roads to Portland tomorrow, my spirits are very high!