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black Box Canyon - Chucksney - Grasshopper Lollipop

  4.5 ( 2 )

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13.8 mile 22.2 kilometer loop


Ascent: 3,152' 961 m
Descent: -3,154' -961 m
High: 5,652' 1,723 m
Low: 2,853' 869 m


Avg Grade: 9% (5°)
Max Grade: 59% (30°)


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Trail shared by Brian Coop

A big backcountry ride leading to the top of an open ridge and a fast technical downhill return.

Brian Coop

E-Bikes Unknown

Features -none-


An old school singletrack climb and descent. Open ridge meadows with huge views of the Three Sisters, Broken Top and Mount Bachelor.

The climb on Chucksney Mountain Trail #3306 is steep, but not technical. The downhill on Grasshopper Mountain Trail #3569 is fast and flowy, but it's punctuated by gnarly rock gardens and a couple rocky creek crossings.

Need to Know

Make sure you're ready for climbing. This route takes the easier Chucksney Mountain Trail #3306 up, but it's still a beast of a climb.


Head up Box Canyon Trail #3660 until it tees into Grasshopper Mountain Trail #3569. Take a left and keep your eyes out for the intersection with Chucksney Mountain Trail #3306 on the right in about 50 yards.

Head right, following the Chucksney Mountain Trail #3306, and settle in for the climb. Just keep on climbing until you reach the top of the ridge where you'll break out of the trees for some amazing views.

Take a break at the top and get ready for one sweet downhill. As you head across the meadow you won't lose much elevation, but once you head back into the trees it starts heading downhill. Keep your speed under control because you tee into Grasshopper Mountain Trail #3569 pretty quickly, then take a left for miles of tight technical downhill all the way back to the Box Canyon Trail #3660 intersection.

Take a right and you've got another 2 miles and 1,000' of smoother singletrack downhill to the trailhead.


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Sep 10, 2018
Tony -d
trail was mostly clear. a couple trees down on grasshopper.

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Trail Ratings

  4.5 from 2 votes


  4.5 from 2 votes
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in Oregon


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3,135 Since Oct 19, 2015
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Brian Coop
Bend, OR
Brian Coop   Bend, OR
You are correct. I'll get that fixed. Jun 2, 2016
Shawn Litson
Oakridge, OR
Shawn Litson   Oakridge, OR
Rode and hiked this three times last weekend...killer! Was with the Disciples of Dirt, Oregon Adventures, USFS, and Modus Sports clearing and reclaiming some extended sections of this trail. We cleared the 4 mile Hiyu Ridge trail that leads to Grasshopper Mountain. We also brushed and cleared the Grasshopper meadow and all the trees from Grasshopper to Box Canyon. As of August 1 thie is golden. Go ride it. ps...we got the dead lizard out of the spring so the water tastes good again. Aug 4, 2016
Brian Coop
Bend, OR
Brian Coop   Bend, OR
Thanks to everyone who got out there and made this trail ready for riding! Aug 4, 2016

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