Having lived here all of my life, I have driven by the large (relatively) parking area at the Angels Rest Trailhead dozens of times, and never really noticed it. In July, King and I packed up early and were the third car in the lot, and started up the hill.
It's an up hike, but, just at the point you're starting to weigh payoff versus pain, the payoff comes in the form of magnificent glimpses of the Columbia River Gorge, and at the top are the most glorious large rock formations and a view to remember forever.
I hiked up to Angels Rest, and crossed over through Wahkeena Springs (sweet spot) to the Wahkeena Falls trail to come back down. The trails are decently marked (take your map anyway as stuff happens), and the only issue was that some idiot neglected to notice that once out at Wahkeena, there was a three mile hike along the Historic Scenic Highway to get back to the van. On a sunny Saturday in July. Very narrow, very busy road, very bad idea - if you're going to do the loop, park a car at both trailheads and take the civilized path back. Otherwise do an up and back. I made it the first two miles and then made the choice for life (actually, King made it - he went down on his belly and refused to continue letting me block him into the nettles) and called a friend to come rescue me.
There are points on the between trail that are going to be marshy when the rains come (if the rains ever come this year), but boot up and you should be fine. Don't recommend this trail if you've been sitting on the couch drinking beer for two years, but if you're in decent shape, you'll love it. Allow four hours for the loop, three for the up and back.
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