FATMAP by Strava

Metolius-Windigo -> Flagline Loop from Phil's


A lengthy loop accessing little-ridden singletrack gems.

Mountain Biking Severe

70 km
1.5 km
1.5 km
6-7 hrs
Low Point
1.2 km
High Point
2.1 km
Metolius-Windigo -> Flagline Loop from Phil's Map

This 43-mile loop from the Phil’s trailhead heads deep into the mountains to the west, accessing little-ridden singletrack trails in one massive effort.


This loop follows a classic series of Bend climbing trails on its way out into the mountains, including the uphill-only Ben’s Trail to Skyliner. Once at the Tumalo Falls Trailhead, the climb continues up the North Fork Trail.

While you’ll begin by passing the astounding vista of Tumalo Falls, North Fork continues to reward with stunning views of thundering cascades in a narrow gorge, views of the rushing stream, and an endless parade of waterfalls as you continue climbing up the trail. While it’s a steep grunt, this is potentially the most scenic climbing trail you’ll ever pedal! The stunning views definitely help the time to pass more quickly.

After North Fork, you’ll continue climbing on Metolius-Windigo, eventually turning in a southerly direction. The Metolius-Windigo trail is a long-distance point-to-point trail running from the Mt. Jefferson Wilderness to Windigo Pass. Unfortunately, portions of the trail run through several different wilderness areas, but on this loop ride, you get to sample a few of the best bike-legal sections.

After several miles of up and down riding along the relatively high elevation sections (for Bend) of the Metolius-Windigo Trail, look for the left turn onto Middle Flagline. NOTE that Middle Flagline is “closed each summer for elk calving until August 15th,” according to BendTrails.com. “Do NOT ride Middle Flagline during this time.”

This means that this loop, as mapped, can only be completed after August 15th. For an alternative route earlier in the year, head around the other side of Tumalo Mountain on the Swampy/Dutchman Trail.

If you do hit the time window right to ride Middle Flagline, you’ll be greeted by "one of the more technical, long and fast downhills in the Bend area,” according to BendTrails.com.

After Flagline, the descent continues down Swede Ridge to Sector 16. Then, you’ll drop into Upper Whoops, on your way to Phil’s. Upper Whoops is a classic singletrack descent that’s actually a fair bit chunkier than most of the trails at Phil’s. Roots and the occasional rock will keep you on your toes throughout, but when you reach Phil’s, the tech mellows out.

The OG singletrack trail in this network still delivers! The classic Phil’s trail has been designated a one-way downhill-only trail, and even without any substantial berms or bike-specific features, this sinuous singletrack offers the perfect kinesthetic bike experience that riders travel the world in search of. The trail rolls along a mellow bench on the side of small hills, dipping and bobbing as it loses elevation gradually but consistently.

In total, your 43 miles of riding will demand 5,000 vertical feet of climbing… and reward with 5,000 feet of descending! This lengthy descent all the way back to the Phil’s Trailhead is to die for!

Sources: https://bendtrails.org/trail/metolius-windigo-trail-99/ https://bendtrails.org/trail/flag-line/



Widely variable, narrow trail tread with steeper grades and unavoidable obstacles of 15in/38cm tall or less. Obstacles may include unavoidable bridges 24in/61cm wide or less, large rocks, gravel, difficult root sections, and more. Ideal for advanced-level riders.

Medium Exposure

2 out of 4

The trail contains some obstacles such as outcroppings and rock which could cause injury.


3 out of 4

Little chance of being seen or helped in case of an accident.

Best time to visit

between August and October


  • Technical
  • Picturesque
  • Singletrack
  • In the forest
  • Roots
  • Rock Gardens

Similar routes nearby

Guidebooks in this area