Elk Cove TH to Timberline Trail
This was an extremely pleasant hike, one of my favorites so far around Mount Hood.
After a short wooded section, you emerge into an area that was burned and is recovering. There's intermittent tree cover, but a lot of the route is exposed.
The views are stunning. You can see the peak of Mount Hood and Coe Glacier ahead along with the Eliot Moraine on one side and Barrett Spur on the other.
There are tons of huckleberry bushes and other vegetation as well as new fir growth, a lot of which encroaches on the trail (pants recommended). There weren't many bugs other than grasshoppers. I only encountered a few flies.
When you reach Timberline Trail, there are meadows, which are magical. The views are breathtaking.
For regular hikers, I would say this route is easy to moderately challenging. The trail is easy to follow—it would be difficult to get off track.
The trail surface is mostly packed dirt. There are no major rocky or sandy sections. There are a couple of steep sections, but most of the way is gradual. There are two small stream crossings. Nearly all of the fallen trees have been cleared (there was only one big one across the trail, but you can step or easily climb right over it).
I was surprised no one else was on this trail. It could be because of outdated reports about trees across the path or needing a high-clearance vehicle to access the trailhead.
As mentioned above, the trail is 99% clear and easy to follow, and nearly any passenger vehicle could make it to the trailhead (in the summer anyway). You should go!