RAMHOOD stands for "Ride Around Mount Hood on One Day". I've been working on this route for a while. It all started with Michael Wolfe's "Mount Hood 217k" that I rode a couple years ago as a "permanent". His route makes the loop via the gorge. Due to the fires in 2017, it's pretty tricky to get through the gorge right now, which got me thinking about finding another way to make that loop. Doing it this way, of course, adds a lot of extra climbing, but also some of my favorite roads in the area.
First you'll roll out via highway 26. The mileage of this ride dictates a really early start, and the highway really isn't so bad early in the morning or late at night. This is at least a 15 hour route for most mere mortals, and you'll probably want to time it so that you're most of the way down the mountain before sunset.
At mile 22 you'll hop onto Barlow Trail Road, and then start the climb up to Lolo Pass. The stretch from here to Parkdale is hands down my favorite road ride in the Portland area. The climb is not too steep, but still pretty damn quick - it took me an hour last time. Stop for a snack at the top, and get ready for a truly awesome descent. About five miles of easy gravel, followed by another ten miles of glassy road carving along the wall of a sweeping valley. You know that picture of Jobst Brandt riding in the alps, looking like a little stick man on his ten speed? I always think of that around here.
And then you're climbing again. It's not super steep, but this stretch in the Hood River Valley is totally exposed. Listen to that Pat Metheny track I posted when you're riding this stretch. That's what I did the first time I rode it, and every time after that. At about mile 75.5 you'll start the climb up to Cloud Cap Inn and begin to regret the day you ever stumbled upon this route. Or you might love it: the view is pretty spectacular.
Most of the climb of to the lodge consists of really shitty dirt road. You'll probably wish you had a suspension fork. But you should ride it on whatever bike you've got. I saw a crew doing it with skinny tires, like 28s. It's short enough that you can just kind of power through.
There's something truly special about having ridden halfway up Mount Hood itself, entirely under your own power. You will have earned the scenery, unlike nearly every other person gazing up at the snowy peak. Have a snack, the descent is not an especially relaxing one. Check out the Cloud Cap Lodge, home base for the Crag Rats search and rescue team. Take a picture to show your friends. Make sure to get some water at the tavern on both the way up and the way down. You'll probably need it.
From here highway 35 winds its way up to Bennett Pass. It's a really nice stretch, and the traffic isn't too heavy even in the summer. Lots of roadies do the ride up to the pass and back as a day ride from Hood River. You'll get some nice views of the surrounding basalt cliffs and of the East Fork Hood River There are a few Robin Hood themed campgrounds just off the highway if you want to try this route as an overnight. I don't know why the campgrounds are Robin Hood themed, this is not especially Robin Hood like territory. It's more River of No Return than Robin Hood.
The descent down from Bennett Pass is pretty fun. The pass sign is just past the overpass for highway 26 (you have to turn around to see it). I like to get photos at pass signs as momentos. Going down, the pavement has some ridges in it, so keep your eyes open. This is a fun stretch to let go of the brakes on. It feels rather dramatic ripping downhill with the mountain peak looming just over your right shoulder.
You'll pass your third Mount Hood pass of the day, Barlow Pass, on your way down to Government Camp. No need to stop here though, you can get supplies in Zig Zag, which is less of a detour. From here it's back to town on familiar roads. I've written before about how much I love Still Creek Road. I'll say it again, this is the nicest friendliest gravel I've ever met. You can tear down this at like 20mph on a road bike if you want.
Then comes Marmot Road, which will probably feel like an insult at this point. Marmot Road consists of a completely unnecessary set of rollers that spits you out at almost the same elevation you started at. You can skip it and stay on highway 26 the whole way if you want, but it's less pretty. I think it's kind of a nice "cool down". Then it's back on the highway for the final 10 miles. I'd recommend listening to slow jams as you ride into the last rays of sunset.