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This well-maintained rolling loop is a treat just minutes from Seattle.

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1,278' 390 m


676' 206 m


690' 210 m


676' 206 m



Avg Grade (3°)


Max Grade (18°)

Dogs Leashed

Features Cave · Waterfall · Wildlife


This is a great 5-mile loop that is easily accessible and well-maintained. An easy route you can exit anytime while enjoying great nature!

Need to Know

A Discover Pass is required to park in Washington State Parks, Dept of Natural Resources and Dept of Fish and Wildlife

Runner Notes

You should get a map (as there are many trails that shoot off in all directions) or use the onX mobile app. Take a wrong turn, and you could make a 5 mile run into a 10 miler (probably good for us). Service can be spotty, so it's best to download the map before you go out.


This is a favorite run that I frequent as it is close to Seattle, has diverse terrain, a challenging hill, and great scenery. It is also the perfect trail to take dogs on as you rarely see people beyond the 1 mile mark from the trailhead.

The loop starts out with a climb on the Cave Hole Trail. This doubletrack trail leaves the Red Town Trail on a slow, steady climb up Cougar Mountain. There are old mining caves in several spots along the trail. The larger of the caves are barricaded and have warning signs around them about the risk of falling or poisonous gasses coming from the ground. Be cautious with small children in these areas. The lush forest growth gives the trail a magical quality as it traverses rocks and exposed roots.

Near the end of the Cave Hole Trail, use the short Bypass Trail to connect to Fred's Railroad Trail. From here, it is a short, gradual downhill to connect to the Shy Bear Trail, a rolling trail that trends downhill for its length to connect you with the Indian Trail. From here, the trail levels out and you have a flat to slightly uphill run back to the Red Town Trail and the Red Town Trailhead.

Flora & Fauna

This area was logged in the early days but has since grown back with classic flora and fauna. On rare occasions, it is possible to see black bears, but they tend to keep to themselves. Cougars have been sighted, but I have never seen one.

Salmon Berries and wild flowers make the Shy Bear portion a great oasis of color and flavor along with a quick view of the Olympics and downtown Bellevue.


Shared By:

Mark Seidl with improvements by Matt Schonwald

Trail Ratings

  4.3 from 47 votes


  4.3 from 47 votes
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in Washington


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The rocky creek running from Far Country Falls.
Apr 10, 2021 near Newcastle, WA
The start of your loop on the Cave Hole Trail is complete with plenty of tall, beautiful trees.
Jun 6, 2017 near Newcastle, WA
Bridge on Shy Bear Trail
Jun 17, 2015 near East Re…, WA
Lots of lush foliage surrounds the Shy Bear Trail.
Jun 6, 2017 near East Re…, WA
The moss is pretty impressive!
May 24, 2017 near Newcastle, WA
Red Town Loop is full of interesting little trailside things, such as this quote from Henry Ford.
Mar 12, 2018 near Newcastle, WA


Current Trail Conditions

All Clear 17 days ago
Add Your Check-In


Dec 6, 2022
Thomas Hollowed
Still coved in snow and ice
Sep 18, 2022
Robert Dean
Jul 15, 2022
Melanie Hodgman
Abby, Julia, and Mel run :)
May 29, 2022
Marie J
Apr 20, 2022
Jennifer Bryan
Apr 3, 2022
Ryan K
Aug 31, 2021
Mark Paluta
May 19, 2021
Joe M
4.5mi — 0h 56m

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