5 Star Route / Ridden and Reviewed by Gravel Girl & Captain “O”

“Too many times, we have buzzed through Madras without realizing that this place is just awesome for gravel riding. This route is just one awesome example of what Madras has to offer. BIG, BIG views of Mt Hood floating in the sky, while you buzz along farm roads. And finishing off with a 27 foot bear stature. Lovely.” Jailbreak by Thin Lizzy

Details: The route starts in Madras and rolls up and out through the Baldwin Hill. We love passing by the cow pastures that lead to the the Hay Creek Ranch with the Great Pyrenees dogs carefully guarding the herds of sheep. (This place was established in 1873 and was a stopping point for the the Dalles Prineville freight and stage coach lines until 1912.). After the ranch, you will reach the Brewer Reservoir which is known to be a great spot for birders. You will continue to climb until mile 18, where you hit Grizzly Road, a super highway for gravel. Then you start to buzz your way back to town, with the big views of Mt Hood unfolding as you go. The route evolves into pavement. Stop to “poke” the impressive bear sculpture past mile 31. The last mile is a short climb, so no whining about us tagging it to the end!

It is best to avoid this route when wet or muddy, because the mud can really stick to your bike. This is a favorite route of ours in the spring and fall.

Adventure / Gravel Route

– Loop: 33 miles / 2400 ft gain
– Mixed route: ~ 85% gravel
– Location: Madras, Oregon
– Rideable: Spring through Fall. Avoid when wet!
– Course by: Captain “O”
– Published: April 2015 (Updated January 2019)


Moderate–. Some punchy hills and a long continues descent.

The Start

Juniper Hill park. Flush toilets.

Food / Water



Cue Sheet / GPX FileTCX File


Red = paved road
Brown = gravel / dirt road

For help with GPS files, the RideWithGPs mapping app and to learn how to download our routes for free, see the “Using Our Rides” page.

5 thoughts on “Jailbreak”

  1. Just rode this today – and it was sweet. Dry throughout and lots of fun! Thanks for the information!

    1. Awesome David. We love Jailbreak except in the rain …..the mud can be horrible. If you have a cool picture, we love to share … mail @ Linda English . Com

  2. May 7, 2017 Ride Report: Riding great! Roads in excellent condition, some rutting after Haystack reservoir. Flowers starting to come out. Fields green. Do not ride when it is wet or muddy – it will become epic in a bad way.

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