Poke the Bear

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 awesome for gravel riding! This route is just one awesome example of what Madras has to offer. BIG, BIG views of Mt Jefferson and the Three Sisters floating in the sky, rolling hills, gurgling creeks, and sprawling ranches. All while you buzz along hard packed, fast gravel roads. And a surprising finish that includes a 27 foot sculpture of a bear. Lovely!

Ride Details

The route starts on the northeastern edge of Madras, climbing for the first 1.25 miles on pavement, then dipping down just as far. Pick up the gravel and roll up and down through the Baldwin Hills for the next 5 miles, gaining a net of 650 feet. Catch the sweeping left banking descent that leads down to Hay Creek Ranch. Pass by the pastures that lead with the Great Pyrenees dogs carefully guarding the herds of sheep. (Hay Creek Ranch was established in 1873 and was a stopping point for the the Dalles Prineville freight and stage coach lines until 1912.) **Click to Read More

Adventure / Gravel Route

– Loop: 33 miles / 2400 ft gain
– Surface: ~ 85% gravel, 15% paved
eBike Friendly: Yes
– Location: Madras, Oregon
– Published: April 2015 (Updated January 2020)


Moderate-. Some punchy hills and a long continuous descent.

When we like to ride this …

In the spring when the creeks flow full and the flowers are in bloom. (Truly our favorite time.) Or on a cool, sunny fall day when the trees are changing colors. Or, on a winter day, when the ground is frozen (yes, frozen, not just cold). It is best to avoid this route when wet or muddy, because the mud can really stick to your bike. Trust us, we have pushed, walked and carried our bikes through ankle sucking mud for at least a mile … which felt like eternity.

The Start

Juniper Hills park. Flush toilets.
Lat / Long: 44.636917, -121.098333

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.

  • Siobhan McNulty says:

    We did this ride on April 20 and conditions were perfect. Encountered a bit of good luck as two of the stretches were being smoothed out/packed down by tractors and the rolling machine thingy.

  • Anonymous says:

    Truly a 5 star ride. April 2020 dirt is riding great.

  • David Smeeth says:

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

    • KevinE says:

      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

  • Linda English says:

    Serious mud for a mile today….the sticky kind. But the rest was sweeeeeeeet. It was after the reservoir.

  • KevinE says:

    Great fall ride also. Conditions excellent!

  • KevinE says:

    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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