Short Version - Wildcat Mountain is only an hour from Portland. You can drive to the trailhead and the two-ish mile hike along a well-maintained, if not well-marked, trail gets you to a small clearing on a summit with wire-ready trees. APRS messaging and 2M FM contacts are both easy and it is a good location for working HF. You are unlikely to be alone, as the Douglas and 781 trails are quite popular; if you like solitude, get there early. And be prepared for snow, even in early November. Note that there are about seven "Wildcat Mountain" in Oregon - make sure you read the right report.
Long Version - Getting to Wildcat Mountain is easy... head down 26 to Sandy and then follow this route: Sandy to Wildcat. The road is paved the entire way though it narrows to one lane as you head up NF105 to the parking area. Take care, it gets icy, especially in the early morning. The Douglas trailhead is well marked and climbs up and around the Wildcat gravel pit where it joins with 781. Follow 781 west about two miles as it climbs roughly 900' and you find the short climb up to Wildcat's summit, 100' higher.
This is a popular trailhead. While mine was the only vehicle in the parking area at 700AM, there were a dozen by 1100AM. Even on a chilly November morning, I passed five or six groups making their way up 781 while I was coming down. There was snow above 4000' and the summit had at least fifteen inches; snowshoes are handy if you don't like postholing. Also note that the trail is not clearly marked and, given the terrain, is easy to lose when snow covered. Stay near the ridge and you are less likely to lose it or miss the cutoff up to the summit. The summit trail isn't marked but is easy to see, as it leaves 781 and climbs steeply to the right.
The summit itself is a small open area surrounded by relatively young, not terribly tall trees. Finding a place to hang an antenna is easy as long as you aren't wanting your wire to be forty feet up. I quickly made nine two meter contacts with five watts and a J pole at ten feet and had no trouble using APRS two way messaging. The summit is HF quiet and there is no noticeable RFI on any band.
While an equipment failure kept me off of HF, I really enjoyed this outing. The hike is a steady slow climb but for the last hundred feet of ascent, there are nice views along the way, and the summit is open enough to allow easy setup. I will come back to do a "settle in for a few hours" activation when the weather is more conducive.