Pinnacle Peak is quite a drive, at which there is no real parking, and no trail, which I suspect is why it hadn't been previously activated - that and the two points. Fun nonetheless, a sense of accomplishment, and some good views to the east.
To get there from The Valley, take SR-22 east past Detroit, to National Forest Development Road 11, a paved and well-maintained, winding serpentine of a road just three miles or so south of Marion Forks, and just past milepost 69. After several miles on NF-11, take a right onto the graveled NF-1133 (it is marked but use a map), followed by another right shortly thereafter onto another graveled road at 44.591451, -122.134607. I'm not sure what this road is called, but you're almost there.
If you look at a topo map, you'll see that about 1/3 of a mile up from the coordinates, you'll be at the base of the most gradual slope to the top. I found a wide(ish) place to park, and blazed my own trail to the peak, with my 12-year old son in tow. A couple hundred feet of elevation gain, some dodgy footing amongst the downed trees and rhodies with a steep-ish push for the last 100 yards, and you emerge at the small rocky outcropping known as Pinnacle Peak.
There are trees in the activation zone to support HF - I stuck with my Yagi-Uda and FT-65 and got Portland fairly easily (and almost got Etienne, too). I was able to activate with relative ease in just about 40 minutes, though there was some interference in the form of ragchew on 146.58 somewhere to the southwest. Still, I got the 4, plus one for insurance, and got to spend some time with my son enjoying the beautiful landscape on a sunny Oregon day.
With a little effort we could see Mt. Hood and part of Jefferson. Three Finger Jack and the Three Sisters were a piece of cake.