Mount Bailey near Diamond Lake is a great hike to fantastic views but it requires some effort to get those views - with a hike of about 10 miles round trip and 3200 feet elevation gain. Like so many summits, it's the site of a former fire lookout with little bits of glass and a few nails the only significant evidence that a building once stood there.
Start at the intersection of Highways 138 and 230, north of the North Entrance for Crater Lake National Park. Go west on 230 a short 0.2 miles and then north 0.7 miles to the South Shore and campgrounds sign where you'll go west for 2.7 miles and go west on NF300. The trailhead is about 0.4 miles along this road near 43.1242, -122.1655.
There is also an upper trailhead described in the summitpost description below but you might consider that it may save you distance and elevation, but not much time. It may require more than 9 inches of vehicle ground clearance and on the upper road there was a parked vehicle with a shredded tire - their spare. Seems like that road could be hard on your car.
The trail can be dusty at the end of summer - especially the lower section. You head up through woods and will cross the road at the upper trailhead after a couple miles and another few miles to treeline where things get a little rocky. There's a simple Class 2 scramble near the summit and lots of loose rock and some exposure after this point, but otherwise no real challenges to this climb. There are some trees for supporting poles for antennas in the Activation Zone below the summit, but none at the high point. I used some rocks to support my antenna at the summit proper - it only fell down four times. There was a bit of 2m FM activity on the Saturday of Labor Day weekend, but none on Sunday, so you may not want to count on just using a HT to qualify for points from this remote peak.
There is nice camping at the south end of Diamond Lake, and there is the Diamond Lake Resort for food and lodging at the north end.
Here's information on the former lookout:
http://www.firelookout.com/or/bailey.html.
You can find additional climb information here:
http://www.summitpost.org/mount-bailey/151169.
