Middle Flagline is closed each summer for Elk Calving until August 15th. DO NOT ride Middle Flagline during this time.
Middle Flagline is one of the more technical, long and fast downhills in the Bend area. The simple fact that this segment is closed for most of the summer makes it a highly anticipated route when August 15th rolls around — it’s pretty much guaranteed that the parking lot at Dutchman Sno Park will be loaded with cars on that morning!
If you are thinking about riding this trail before it officially opens on August 15th, think again. The trail will be riddled with deadfall, and there is a full time Forest Service employee roaming the Bend Watershed in the summer.
While you can climb Middle Flagline from Swampy Lakes to reach the Metolius-Windego trail, 90% of riders will start at Dutchman and head downhill towards Bend. The popular “Bachelor to Bend” shuttle usually includes the Middle Flagline trail.
Another popular way to access Middle Flagline is to start at the Skyliner Sno Park, climb Northfork to Met-Win and loop back to your car — that route combines lots of XC climbing with ripping fast DH.
This trail is maintained by Central Oregon Trail Alliance.