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Box Canyon - Chucksney - Grasshopper Lollipop



13.8 mile 22.2 kilometer loop
100% Singletrack


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

Electric Mountain 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 14, 2019
Stefano Pellerano
Excellent conditions. Super grippy. Teeth shattering downhill. Stopped for lunch on the top (included in time above) — 6h 20m
Sep 10, 2018
Tony -d
trail was mostly clear. a couple trees down on grasshopper.

Trail Ratings

  4.3 from 3 votes


  4.3 from 3 votes
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Ride Rankings


in Oregon


38 Views Last Month
3,661 Since Oct 19, 2015



We had to take a break on the amazing downhill to take in all the glorious fall colors.
Sep 30, 2015 near McKenzi…, OR
There are still some wet places in Western OR, even in a dry year.
Sep 30, 2015 near McKenzi…, OR
There's some chunky goodness on the downhill.
Oct 19, 2015 near McKenzi…, OR
At the top of Box Canyon Trail!
Sep 30, 2015 near McKenzi…, OR
Grabbing some lunch after the climb with amazing views of the Three Sisters, Broken Top and Mt. Bachelor on the horizon.
Sep 30, 2015 near McKenzi…, OR
Peek-a-boo views of the Three Sisters
Sep 30, 2015 near McKenzi…, OR

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