Distance: 41-mile lollipop
Elevation gain: 3820 ft

This ride is expertly covered in Jim Moore’s 75 Classic Rides Oregon (see the “Oregon” section in Rides by Region).

This is a varied, largely open ride with grand vistas of the Columbia River Gorge, a sweet stretch of old highway closed to cars, a jaw-dropping descent through a comically extreme set of switch-backs, and one strong dose of good old back-country climbing.    It’s about the landscape—I don’t find the road contour or the two communities you pass through (Mosier and the Dalles) terribly compelling.  The route is easier to follow than it sounds—as they say in “Willow,” “Ignore the bird, follow the river!”—unless you miss the turn onto Chenowith Loop W., you really can’t get lost.  

(To see an interactive version of the map/elevation profile, click on the ride name, upper left, wait for the new map to load, then click on the “full screen” icon, upper right.)

https://ridewithgps.com/routes/37934016

Ride east out of Hood River on Old Columbia River Drive.  Right off the bat, climb up to the old highway and your hard climbing is done until you start the return trip from the Dalles (rhymes with “pals”).  The road soon becomes a flat recreation path closed to cars—very quiet, very pretty.   The path dead-ends on Rock Creek Rd. just west of Mosier.  Go L on Rock Creek Rd. into Mosier, a full-sized town with all services, and through town on 1st Ave (the main street) and continue as it becomes Hwy 30, Mosier-Dalles Highway.  Climb up from the river until a few miles east of Mosier you come to the top of a high bluff.  Take a moment to drink in the view—both the view north out over the river and the view southeast looking down on what you’re about to ride—and drop down the back side through a ridiculous series of switchbacks called the Rowena Loops.

Continue on to the outskirts of the Dalles.  Go R on Chenowith Loop W (watch for it—it isn’t prominent), quickly turn R on Chenowith Rd., and go R fairly soon on Seven-Mile Hill Rd.  The name doesn’t lie.  Climb moderately for seven miles and stay on the road as it descends pleasantly through a number of road name changes you can ignore and returns to Mosier.  Return to Hood River the way you came.

Shortening the ride: Ride to the Rowena Loops; decide if you want to descend them and ride back up; return the way you came.

Adding miles: The Hood River Valley to the south of the town of Hood River is a famous network of excellent cycling roads, and you can wander on either side of Hwy 35 and find great riding.  The roads on the east side of 35 are particularly nice.  However, the area is famous for smoking winds (Hood River is a world-famous windsurfing and kite surfing mecca for a reason), so expect to have your brains blown out.   A short car trip to the west on Hwy 84 is another stretch of old highway paralleling 84, this one passing by Multnomah Falls and the other famous falls of the Gorge, Vista House, and lots of other goodies.   This one isn’t closed to cars—in fact you’ll swear that every car in Oregon is on it—but the scenery is justly world-famous.  Bring shoes to hike the falls trails.

Afterthoughts: The infamous winds of Hood River can be a monkey wrench on this ride as well as in the valley.  The prevailing direction is out of the west, so check the weather report and expect a headwind on the return ride, especially from the Dalles to Mosier.

The Mosier-to-Dalles loop can be ridden counterclockwise, the only drawback being that it transforms the Rowena Loops from a thrilling steep descent into a somewhat-less-thrilling steep ascent.

Old Columbia River Drive isn’t open to cars, so some maps and mapping sites don’t acknowledge its existence.  Trust me, it’s there, and you won’t be alone.