This is certainly a gem of a ride.
The Flagline trail can be accessed via Dutchman Sno-Park.
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 (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, officially the Flagline trail. 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.)