O'Leary Mountain Tr3321 is a steep ridgeline ascent to MacDuff Mountain.
Check forest service road conditions, as FR1993 access is affected by washouts and other damage and the upper TH may not be accessible by car. O'Leary Tr3321 can become overgrown when riders are not able to shuttle from the upper Olallie Tr3529 TH (due to FR1993 road closure).
The O'Leary ridge trail traverses three mountain peaks: Mclennen, Macduff and O'Leary mountain, with a steep 4mi ascent between the TH and Mclennen mountain.
All of the trails to the east and south of FR1993 are in wilderness areas.
Too steep to be ridden OAB, from the FR411 trailhead O'Leary Tr3321 has a 4mi, 14% ascent to MacDuff Mountain. Ascending Olallie Tr3529 (or FR1993 if possible) to the upper O'Leary Tr3321 TH is the only reasonable option, making this a ride best left to shuttling.
With most of the climbing on FR2639 and FR1993, ascending a 1.5mi (10% grade) section of Olallie Tr3529 instead of continuing on FR1993 is manageable. Check on the FR1993 road condition, as it is prone to closures.
The 7mi (1900' ascent) FR2638-FR1993 road ride could be avoided with a shuttle, but is a reasonable ascent.
TH: From the King Castle Tr4326 TH, go east on FR2638 to the 3.8mi FR2639 intersection, then go right, to the 4.2mi FR1993 intersection.
4.2mi: Ascend FR1993, with an option to continue ascending FR1993 from the 7mi Olallie Tr3529 intersection to the upper FR1993 intersection. Do what you can.
10.4mi: If ascending Olallie Tr3529, then go right on O'Leary Tr3321 and enjoy the wild descent to the O'Leary TH
View of the O'Leary Trail 3321 TH.
18.5mi: Go right onto Castle Rock Tr3506, with a moderate descent to King Castle Tr4326, then a great downhill run to the TH.
East Fork Tr3308 is in the Three Sisters Wilderness Area and East Fork-Ollalie Connector Tr3326 is not suitable for biking, so this challenging CCW loop is best suited for hikers.
As a CCW loop, there is a 2mi, 16% ascent on the East Fork-Olallie Connector Tr3326.
Nearby Walker Creek Tr3330 follows the Walker Creek drainage on an ascent to Lowder Mountain. The trail is infrequently maintained, so may be hard to follow at times, requiring backcountry navigation skills.
Lowder Mountain Tr3329 offers views of the French Pete drainage on the way to Yankee Mountain, descending 3900' in 4mi, past the old Tipsoo Butte lookout site through many steep switchbacks to Cougar Reservoir. Trail may be difficult to locate through the meadows area.
The 2mi Quaking Aspen Swamp Tr3332 is a nice short day hike, passing Quaking Aspen Swamp Botanical Area and Aspen Creek.
Echo Trail 3309, Olallie Trail 3529, O'Leary Trail 3321
East Fork Trail 3308, East Fork-Ollalie Connector Trail 3326, French Pete Creek Trail 3311, Lowder Mountain Trail 3329, Quaking Aspen Swamp Trail 3332, Walker Creek Trail 3330, Yankee Mountain Trail 3318
Cougar Crossing Campground, Horse Creek Campground, Limberlost Campground, McKenzie Bridge Campground, Paradise Campground, Slide Creek Campground, Sunnyside Campground
Ranking consistently applied to all of the listed trails.