Shy Bear
Issaquah AlpsBest Year-round
A forest ramble through Cougar Mountain's southern heart, passing marshland and connecting to waterfalls.
About This Trail
Shy Bear runs 1.5 miles through the southern interior of Cougar Mountain Regional Wildland Park, threading between Shy Bear Marsh, Longview Peak, and a web of trails that reach waterfalls, old coal mining remnants, and a handful of viewpoints. The forest is dense second-growth, with enough canopy to hold off light rain and enough understory to feel genuinely wooded rather than park-like.
The trail is a backbone for longer loops. A well-loved circuit links Shy Bear with the Wilderness Peak Trail, Deceiver Pass, and Doughty Falls for about 5 to 7 miles depending on how many side trails you pick up. Far Country Lookout sits roughly 1,000 feet from the trail's western end and is worth the short detour. Birders appreciate the marsh area, where the habitat shifts from upland forest to wetland edge.
Access works from multiple trailheads, including Sky Country, Redtown, and Jim Whittaker Wilderness Peak. Weekend mornings see steady traffic, especially at Sky Country, but the trail itself absorbs people well. Mud is a constant companion from fall through spring. Blowdowns crop up after big storms, but the volunteer maintenance crew keeps things passable. No pass required at any of the access points.
Astronomy
Trail Conditions
“no snow on the trail but there was a dusting on the woods.”
Last report: Apr 12, 2026
Scorecard
Safety & Considerations
Today's Hazard
- Strong sun — sunscreen, hat, and sunglasses recommended
Persistent Hazards
- Muddy trail conditions fall through spring
- Occasional blowdowns after major storms
Getting There
Multiple access points. Sky Country Trailhead is the most common start (spacious lot, restroom, no pass required). Also reachable from Redtown Trailhead or Jim Whittaker Wilderness Peak Trailhead. Weekend mornings can be busy at Sky Country by 9 AM.
From Sky Country Trailhead, follow Old Man's Trail or Bypass Trail to reach Shy Bear. From the east, the Wilderness Peak Trail connects at Shy Bear's eastern end. The trail runs point-to-point with junctions at both ends, making it a natural loop component.
Early weekend starts recommended to secure parking at Sky Country. Weekdays are reliably quiet.
Recent Reports
Walked the Cougar Mt trails out to the top of Wilderness Peak as kind of a defacto memorial for Jim Whittaker who passed this last week since he is the namesake for the Wilderness Peak trail. Parking at the Red Town is free though can fill up quick however only a dozen or so cars at quarter to 8 and only 2/3rds full at 12 with plenty of spaces left.
This trail never disappoints. Morning fog left the trail a tad muddy in places but we encountered evidence of removed trees (from blow downs) and no diversions on our loop including Gombu-Whittaker Peak-Shy Bear Pass-Deceiver Pass-Doughty Falls.
My hiking group switched gears when it impossible to get to our planned hike Greenwater Lakes hike due to a road closure. We started from the Sky country trailhead at 9:00 AM, 3 cars were in the lot when we pulled up.
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