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O'Leary Trail Loop - IMBA Epic

 12 votes

19.1 Miles 30.8 Kilometers



4,474' 1,364 m


-5,795' -1,766 m


5,111' 1,558 m


1,238' 377 m



Avg Grade (6°)


Max Grade (24°)

All Clear

5,111' 1,558 m


1,238' 377 m



Avg Grade (6°)


Max Grade (24°)

Endless backcountry adventure with narrow trail and a stellar final descent.

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Featured Ride


Open mid-spring through late fall. Check with locals for snow conditions and removal of downed trees.
This ride is the burly, backcountry brother to the nearby and more famous McKenzie River Trail (MRT). While the MRT offers easily accessible singletrack, the O'Leary Trail Loop serves up endless backcountry adventure with narrow trail hurtling into tight switchbacks, rock walls built decades ago by the Civilian Conservation Corps, throttling climbs, and a final descent that makes you forget the pain.

Need To Know

Although both trailheads are accessible by vehicle, a good way to link the two is to ride from the Kings Castle trailhead east on King Road/National Forest Road #2639, and then climb south on National Forest Road #1993 to the Olallie North trailhead. Starting the ride from nearby McKenzie Bridge offers restrooms, parking, and food/beverages. Going big with this route adds several pavement and gravel road miles, but more importantly puts the total climbing near 6,000 vertical feet of leg-searing ascending. Ah, but the payback....

This ride requires fitness, skill, and the ability to keep your cool in a remote, backcountry setting. If you break your ankle in the middle of this ride youll be spending the night before search-and-rescue can come retrieve you for your heli lift. Dont do this ride alone and choose your crew carefully.


From the Olallie North trailhead on National Forest Road #1993 head south on Trail #3529. The climbing starts immediately; get used to it. After what seems like too long surrounded by tall trees and leafy rhododendrons the trail will cross National Forest Road #340, and you can take solace that youre about halfway up the mountain.

Not too far past the road, turn right onto Trail #3321 and out towards the ridge. The landscape changes and the trail gets narrower, more rugged, and rocky. Youll pass the high point next to McLennan Mountain but wont get a break until youve switchbacked up to Macduff Mountain. Stop here, scramble up the scree slope, and savor the view of the Cascades.

The trail finally heads downward, and with a vengeance. The vertical peels off the altimeter as wildflowers and views fly by, but dont take your eyes off the tread for a moment because the only predictable part of the ride is that it is unpredictable. Sharp turns, rocks, bear grass obscuring the trail, and nonchalant porcupines are standard fare.

After passing a large segment of rock retaining wall that was built during the Great Depression the trail crosses National Forest Road #411; dont miss the barely discernible tread as it heads back up the hill on the right side of the road. The trail again takes a nosedive on an old-school descent that will have you wondering how people ever rode mountain bikes before disc brakes and dropper posts.

After crossing National Forest Road #411 for a third and final time keep your eyes peeled for the intersection with Trail #3506, which will sneak by as you float through the emerald woods. Turn right and head past eight-foot diameter Douglas fir trees while catching a break along this rolling segment before climbing to the intersection with Trail #4362.

Payback time. Ingest some sugar, shake the lactic acid from your legs, and get your flow on as you twist though a moss-encrusted forest on a trail that looks like it was tailor made for your weary body. Once youve whooped and hollered one last time at Kings Castle trailhead it is time to roll into McKenzie Bridge and eat a large meal of gluten, dairy, and meat, because youve earned it.

History & Background

The Civilian Conservation Corps built part of this trail in the 1930s during the Great Depression. Also make sure to check out the bronze plaque at the top of Macduff Mountain that commemorates Nelson F. Macduff who was an early forest supervisor.


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4.8 from 12 votes

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Sep 4, 2016
Stefano Pellerano
Sep 4, 2016
chris streight
Road from McKenzie Bridge, which makes it 29.46 & 5600'. Trail is in very good shape. Couple downed trees on Kings is all. Had the trail to ourselves 29.5mi
Oct 19, 2015
Mark Peternell
Sep 6, 2015
Brian Kennedy
What a ride. Probably the best I've ever done. Very challenging climbing and descending, but worth the payoff. 19.7mi — 4h 10m
Aug 17, 2015
Brian Coop
Did the whole loop starting at the Castle Rock TH and riding the road up to the O'Lallie TH. O'Lallie is steep enough it's nice to have a warmup. 25.5mi — 5h 40m
Aug 15, 2015
Brennan Morrow
4 trees down on east section. switch back on west side are being reconstructed 27mi — 4h 00m
Apr 20, 2015
seth swallen
26mi — 5h 30m
Mar 28, 2015
geraldine aron

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Trail Ratings

  4.8 from 12 votes


  4.8 from 12 votes
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All Clear 31 days ago
Mostly Dry, Fallen Trees: The revamped trail is incredible!!! Maybe two trees down, but easily avoidable. Pristine otherwise.
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Forecasting the weather...

Truly epic!!! Hard, rustic, exposure sections and beautiful! If you want to bypass climbing (a real grinder), shuttle up to O'leary by-passing O'llalie... Great reward at the end.... again, Epic... Jun 14, 2015

There's lots of trail work going on on O'Leary this season, partnership between Horse Creek Lodge & local forest service, so might be good to give us a call at 541-822-3243 or the Ranger Station at 541-822-3381 before you go. Jun 27, 2015

Cog Wild is definitely sending people this way, which is great! We were awarded a grant to make a lot of improvements so we're working w/our local Forest Service, DOD, GOATS and COTA to make the needed improvements. Northwest Youth Corps is out as of late June working on this trail, so expect to see some flagging and possible re-routes this year and next. Jun 27, 2015

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