City Escape: Ashland, Oregon

Buried between the remote Siskiyou and Cascade mountain ranges just north of the California state line lies the charming town of Ashland, OR. This burg’s location, far from any major city, is probably the greatest part of Ashland’s allure—Portland is about 300 miles to the north and San Francisco is the same distance in the other direction. 

But that remoteness, along with the region’s mountainous topography, is the reason you’ll find a good number of fantastic, traffic-free motorcycle roads in the area.

One of the best roads out of Ashland is a two-lane ribbon of blacktop known as SR 66. It wends its way south and east out of the downtown area before squirming into the nearby wilderness of the Rogue River-Siskiyou National Forest. 

In addition, there’s another twisty thoroughfare to close the circle—Dead Indian Memorial Rd. All told, the entire loop runs about 100 miles and should take you around three hours to navigate, depending on stops and road conditions.