Shy Bear

Issaquah Alps

updated 6 days ago

The trails on Cougar Mountain, specifically Shy Bear, are in good condition as of September 19. The roads are suitable for all vehicles, and there were no significant bug issues reported in late August or mid-September. Some minor obstacles like dislodged rocks were noted, but they were not major concerns. Water levels in the creeks are very low, with only small trickles observed, and waterfalls are not flowing. While fall colors have not yet arrived, the woods offer a pleasant experience.

Generated from 37 trip reports. Trails change faster than reports do, so check anything you’d turn around for.

What hikers ask about Shy Bear

Generated from the most recent trip reports, newest 6 days ago. Check anything you’d turn around for.

The road to Shy Bear is suitable for all vehicles as of September 19. This condition has been consistent across recent reports in late August and mid-September.

More in Issaquah Alps

Trail notes generated from recent reports. Conditions change fast.

Sources

Issaquah Alps > Cougar Mountain

This was a pleasant hike up to Long View peak. The elevation gain wasn't too bad, the trails were well maintained, though Indian trail was a bit more of a rocky road. Once getting onto Shy Bear and De...

Issaquah Alps > Cougar Mountain

Great choice when short on time but need a hike with a bit of cardio and soul enriching lovely woods.No fall colorsyet. Arrived Noon to be only car at the plentiful roadside parking area. Sign is smal...

Issaquah Alps > Cougar Mountain

Today's #hikeathon 2026 outing was intended to be Lower Tuscohatchie Lake (14 miles/4400') with 9 members of the Seattle Mountaineers CHS-2 cohort, but AQI was abysmal and after 2 minutes of talking w...

Issaquah Alps > Cougar Mountain

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...

Issaquah Alps > Cougar Mountain

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 Pe...

Issaquah Alps > Cougar Mountain

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 wh...

Issaquah Alps > Cougar Mountain

Short hike first thing on a drizzly Saturday to decongest thoughts and get some overly fresh air. Parking was already busy at 9.30. The trail network was expectedly wet but not too muddy. Coal Creek F...

Issaquah Alps > Cougar Mountain

great day for a hike. no snow on the trail but there was a dusting on the woods. only saw s few others on the trail

South Cascades > Goat Rocks

1/21/2026 · Longview Peak & Far Country Lookout LoopParking:Parking lot had a few cars, very quiet and seemed pretty clean and maintained.Route:Sky Country Trailhead → Old Man’s Trail → Bypass Trail →...

Issaquah Alps > Cougar Mountain

The virgin forest on Deceiver ridge is so beautiful on a misty day.  The trail has a few mud holes but overall is in good condition. Doughty falls was running well but only about 1/2 the flow as it wa...