Brian, that trail looks like a game trail/user trail. There doesn't seem to be any dugout tread or blazes on trees, or at least from what I can see in the photos. Does this trail go down to the main branch of the Clackamas River?

Here's the tread in the second shot, as said, this land was logged heavily, but before I was born

In looking at the 36 pit fire map, the fire got mighty close to the old trail. 

If it matters, just to my left in the first photo is a substantial waterfall on a well known creek. 

You could access a lookout from this trail

Head across the Clackamas River.

Hint: There's a road named after the body of water with the waterfall I mentioned.

This is the trail along the North Fork Clackamas River to Bedford Point. This spot was up past Fall Creek just before Bee Creek where the trail and flags turned and headed up the hill