5 Star Route / Ridden and Reviewed by Gravel Girl

“Tonight there’s going to be a jailbreak. Somewhere in this town. See me and the boys we don’t like it. So we’re getting up and getting down.” Jailbreak by Thin Lizzy

On this ride, you go by the Deer Ridge Correctional Institute. But there’s a lot more to this route besides a possible jailbreak … you wander through the majestic Baldwin Hills with glorious views of the mountains and past a historic sheep farm. (We always love to watch the the Great Pyrenees dogs tending to the herds of sheep on the Hay Creek Ranch. This ranch was established in 1873 and was a stopping point for the Dalles-Prineville freight and stage coach lines until 1912.)

The first 16 miles rolls up and over the hills through wild country and past scenic farms. At mile 19, begin a long descent back to Madras with outstanding views of the Cascades Mountains to the west.

It is best to avoid this route when wet or muddy. 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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