Summary - About two hours from Portland, Squaw Butte is an easy drive, hike, and bushwhack to a forested summit. There are limited views, trees for wires, and a number of good operating positions. Two meter contacts are likely to be difficult, as is spotting with a cell phone; APRS works okay. Google maps gives good directions. Pair this one with West Twin Butte.
Long Version - Squaw Butte is one of a cluster of summits reached through Carson, Washington. Google will direct you via Wind River highway, FR30 and FR24, which works. The drive is about 90 miles from Portland and almost all on paved roads. The trailhead (Squaw Butte #21) is on the edge of the Tillicum Campground. I was there in October and had the place to myself; in season, finding a place to park might be more challenging.
The trail is through open forest, easy to follow and a gentle climb. At roughly 46.114, -121.797 you will find a faint trail heading WNW. I lost the trail pretty quickly, took a bearing on the summit and just headed uphill in the right direction. The bushwhack is through open forest, so not much of a challenge. You know you missed the summit trail if you start going downhill again! The hike is about 1.5 miles and climbs roughly 1000 feet.
The summit is flat and forested; views are limited. It is easy to set up antennas and find places for multiple operators. Two meter contacts into urban areas are likely to be difficult given the topography and distance. Digital cell service (ATT) was spotty, APRS connections good.
For an easy two summit day, see this brief on West Twin Butte.