#8: Freebridge Road • 3.5 mi • 857 ft

Freebridge Road is named after a free bridge across the Deschutes River that Wasco County constructed in 1887 as an alternative to the nearby toll bridges. Apparently the toll bridge owners didn’t like the competition, because in 1914 the bridge mysteriously “collapsed in a windstorm” — but many say it was more likely dynamited intentionally.

The concrete supports still sit in the middle of the river today.

The remaining road climbs out of the Fifteenmile drainage and over the hill to the top of the Deschutes box canyon, then plummets down to the river on a harrowing, 4-wheeler doubletrack with lots of exposure.

Enterprising overlookers can probably find a nice view from the top of the canyon if they take off their helmets and put on their thinking caps for a minute.