I was driving back to Portland from Northern California and taking Highway 97 for the scenic beauty. There are a number of 4 and 6 point summits in the region with easy-ish access, so I thought I'd try one or two along the way. A forest service employee recommended Orr Mountain, which has great views, a nice open area at the top and an active fire lookout.
Flagtail Mountain is not close to any population center. You can get to it from John Day by traveling south on US-397 and then turning west onto Izee Paulina Lane. Travel this paved road to 44.1618, -119.2511 and turn onto a good gravel road. Drive about five miles to an active lookout.
Camel Hump is a summit out of St. Regis, Montana on the Interstate 90. From St. Regis you have about a 7 mile drive on paved roads, then about a 6.5 mile drive up Forest Service road 3800. At that point you encounter a closed gate but it's an easy 1 mile walk to the summit from here. Please refer to my saved map in the link below. You do not need a four wheel drive on this road, any car can make it easily.