Pleasant Ridge is so many things: a twisty tarmac climb just outside of town, the best gravel descent in Wasco County as it drops into Fivemile canyon, a waterbar-crossed blast out of Mount Hood National Forest, and apparently a ridge somewhere that is pleasant to behold.

Depending on what map you look at, Pleasant Ridge Road might be called Jewel Road or NF 4440 at the top, and might include a connecting section of 5 Mile Road to connect to the lower Pleasant Ridge.

This mystical twisting ribbon of tarmac follows 8 Mile Creek from its confluence with Fifteenmile all the way up into the hills above Dufur, where it straightens out and turns to dirt in a pleasant, pastoral valley—before turning into Walston Grade and climbing from out of the river valley and up to Pleasant Ridge.

I have fond memories of racing down the twisty tarmac section in rotation during the old Gorge Roubaix road race.

Like the other whatevermile creeks, Eightmile Creek was named after its mile marker on the Oregon Trail from the end of the road in the Dalles. The road connects to about 10 other great roads, is a dream uphill or down, and can be used to loop together any number of great rides.

If The Dalles had a Greatest Hits album, half the songs would be called Somethingmile Road. Threemile is one of the absolute classics. Starting just outside town, Threemile traverses a couple beautiful orchards on its way to its namesake Threemile Creek, then bends upward, locking in its course directly toward the top of Mount Hood. The little idyllic, pastoral valley tightens up as the road climbs, until the ranches go away—replaced by rock shelves, oak and pines. Eventually the road crosses Dutch Flat, Threemile Creek trickles away, and the road changes to a national forest road, and climbs up to the 44 Trails area and Surveyor’s Ridge Road.

It’s yet another amazing, super-long Dalles road that climbs from down low in the dry Eastern Oregon grasslands through a wooded valley all the way up to Mount Hood National Forest — what more do you need?

Similar to Three Mile, 5 Mile follows its namesake creek. It also has rock shelves — tons of ‘em. Unline Three Mile, its creek keeps going all the way to Mount Hood National Forest, so you stay down low in the valley for a long time. 

Another great way to climb up or descend to or from Skyline, 5 Mile, Pleasant Ridge, or just keep going forever into the Forest.

I have no idea why this road is named Japanese Hollow, but I believe there are some cherry trees along the road. If you know the history, drop me a line.

I learned about Japanese Hollow as the namesake of OMTM’s excellent Japanese Hollow loop, which routes you up Japanese Hollow so you can go down the magnificent Pleasant Ridge descent.

Apart from its unusual name, Japanese Hill is a similarly bucolic half-gravel road to its neighbors. It climbs up a nice valley with some scrubby trees — first gradually on pavement, then steep gravel.

Sure, you could say that Center Ridge Road is just a road on top of a ridge that’s half-paved, half-gravel, and connects a bunch of other roads together. And you’d be right.

But Center Ridge is definitely noteworthy on its own on its own. It traverses a high triangle between the watersheds of the Deschutes River, the White River and 15 Mile Creek — and you can see for many, many miles in every direction. On a good day, you can see Mt Jefferson, Mt Hood, Mt Adams, Mt St Helens, Mt Rainier and Goat Rocks. On a bad day, it’s hot or windy or cold or storming or all of the above.

Mill Creek departs from more or less the center of The Dalles, follows Mill Creek into a forest, then ascends all the way to the the top of the ridgeline above.

The road is mostly an easy spin along the creek. Eventually the pavement ends… “and the West begins.” Continue through onto Mill Creek Ridge road if you want to exit human civilization for a world of four-wheeler tracks, shotgun shells, abandoned cars. I once stopped early into a ride on Mill Creel at the Sandoz Farm stand and bought teriyaki pork jerky. I was glad to have it, hours later, as I lugged my bike over tree after tree on Mill Creek Ridge.

Chenowith Road has three distinct sections. The bottom mile or so it’s a busy (by Dalles standards) road to the town of Chenowith. The next couple miles are tranquil tarmac in a nice valley next to an improbable miniature airport. As soon as the pavement ends, about halfway, the road turns brutally steep, and the surface gets loose and rocky.

I make a point of only riding down the steep part of Chenoweth as it drops into town from Ketchum Road. It’s tough enough going down — I can’t imagine what it’s like going up. But if you want to get up to the beautiful, ridge-top savanna of Ketchum as directly as possible, this is the way!