Shevlin Park to Phil's Trailhead via Flagline

Dogs Unknown

E-Bikes Unknown

This is a big ride with lots of climbing, great views, and a long downhill. There are some technical sections throughout and some jump/flow sections on the downhill (Whoops). I've rated it Intermediate/Difficult due to the distance and climbing, but the majority of the trails are Intermediate.

Shuttle from Shevlin Park to Phil's Trailhead or ride the whole thing from most anywhere in Bend (for an extra 8-10 miles on the road).

Park at Shevlin Park (and shuttle a car to Phil's Trailhead) and take the north side of the Shevlin Park Trail to Mrazek.

Take a right and climb up a series of technical switchbacks to get up out of the canyon. Mrazek then settles into a long climb up smooth singletrack with one or two short steep technical climbs and periodic views and lookouts until you meet up with Metolius-Windigo.

Take a left onto Metolius-Windigo and ride across some small creeks until you cross the bridge in Happy Valley. Take a right after the bridge to stay on Metolius-Windigo and some steeper climbs through a deep pine forest. Just as you're getting some great views of Broken Top, you'll hit more rolling terrain and then drop down a few hundred feet where you'll intersect with Flagline.

Take a left on Flagline towards Swampy Lakes and get ready for some more climbing as you roll through more pine forest and some alpine meadows. In a couple miles you'll finally roll over the top and start a super fu, flowing downhill with some rocky technical sections thrown in to keep you on your toes. Pass by Flagline Tie and in a mile or two take a left towards Swampy Shelter.

Stay straight as you pass the shelter and you'll cross a technical stream crossing, then take a left at the next intersection towards Swede Shelter. You'll roll up and down on some combination technical and flowing singletrack until you reach the shelter - stop here for a snack and some great views across the canyon of South Sister and Broken Top.

Now just stay straight onto Sector 16 for a couple miles of rolling singletrack to the shelter at the top of Upper Whoops where more views of the Sisters await just on the other side of the shelter.

This is where it all heads downhill, fast. Upper Whoops is a screaming flow trail with banks and a couple little jumps. When you reach the bench/feature at the next intersection, ride straight across to enter Lower Whoops.

Lower Whoops is a two-mile stretch of tabletops, banked corners, and some little doubles. It's one-way down, but keep your ear out for people coming from behind. You've got to ride it fast to clear the jumps, but it's totally good to just roll it at a lower speed until you gain the skills. At the bottom of Lower Whoops, take a right on EXT Trail for a new connection to get to Phil's on the left.

Once you enter Phil's, it's pretty much all down hill to the trailhead. The first few miles are two-way, but it's clearly signed where it starts one-way and you can let it all hang out on the swooping corners and a bit of tech through Phil's canyon. Go past (or over) the rocks at the flaming chicken (miniature version of the sculpture at Galveston/14th circle in town) and there's just two miles left. When you get to the trailhead, congratulate yourself and anyone else that came along for completing one epic adventure!