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 13 votes

12.1 Miles 19.5 Kilometers



1,340' 408 m


-1,336' -407 m


6,960' 2,122 m


6,108' 1,862 m



Avg Grade (2°)


Max Grade (9°)

Minor Issues

49 days agoUpdate

A great loop featuring the Flagline trail with a sweet descent and plenty of challenging features

Katy Ryan


Generally closed until ~ Aug 15 every year for elk calving grounds.
A gem of a ride with a grind of a climb through forested slopes to reach a ripping descent down Middle Flagline and Flagline Tie.
Dogs: No Dogs

Need to Know

The Swampy Lakes trails can easily extend this loop. As well, your ride could end at Swampy Lakes Sno-ParkTrailhead if you set up a a shuttle.


Accessing Flagline from Dutchman Flat Trailhead (as described here) makes for a much shorter ride (v. access from Tumalo or Skyliner trailheads). The ride begins with incredible views of Broken Top and the Cascade mountains. It then heads east into a forested uphill section to follow Middle Flagline. After the uphill grind (and it is), you are rewarded with all the sweet and challenging features ever imagined. Keep your focus, and your hands on your bike at all times. Now just go!

The first intersection you reach will be the Flagline Tie, which will eventually lead you back to Dutchman. The fun continues on the Flagline Tie, though much easier than Flagline proper. Soon you encounter another intersection, that leads you back to Dutchman, where it all began. You didn't think you could have all that fun downhill without a little uphill return? (I suppose you could have a car parked at Swampy trailhead, then shuttle.)


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   Clear Rating

4.7 from 13 votes

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Oct 2, 2017
Chris Bailey
Turned back due to too much snow. 3mi
Aug 29, 2017
Michelle Larsen
Aug 16, 2017
Karl Topping
2 wrong turns & 1064 calories burned 20.4mi
Jun 28, 2017
John Mcilmoil
We turned around at the calving grounds but there was so much snow there you couldn't see the trail.
Oct 14, 2016
Paula Churchill
Always great! 20mi
Oct 7, 2016
Mike Powell
Sep 24, 2016
Lizz Robnett
Aug 25, 2016
Matt Moss

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Trail Ratings

  4.7 from 13 votes


  4.7 from 13 votes
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in Oregon


69 Views Last Month
9,361 Since Sep 26, 2012
Intermediate Intermediate



Minor Issues 49 days ago
Snowy - I turned back today due to too much snow as you got higher up.
Update ConditionsHistory

Getting forecast...

Dutchman to town is a Bend classic with many optional routes. Flagline, South Fork, Whoops, and finishing with Phil's gets a lot of gems in one ride. Aug 19, 2015
Taylor Cullum-Muyres
San Luis Obispo, CA
Taylor Cullum-Muyres   San Luis Obispo, CA
Great ride. A few steep loose, spots in the initial cilmb, Awesome downhill that offers different lines with varying levels of technicality. The last 3 miles is old decommisioned double-track and very sandy in spots. Aug 22, 2015

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