Pine Mountain (W7/CN-058) (2 miles RT and 500 feet) and Pine Benchmark (W7/CN-068) (~3 miles RT and 600 feet if you walk the road) are close enough that one could easily do both summits in a day. They have good views and are not far outside of Bend and if you spend the night at the summit campground you might check out the telescope at the Pine Mountain Observatory (http://pmo-sun.uoregon.edu/).
Take Highway 20 east from Bend and find the sign to Pine Mountain Observatory just past the (closed) Millican Store near milepost 25. Pine Mountain Road is a good gravel road for any vehicle.
For Pine Mountain, at about five miles, look for a three car pullout near 43.792, -120.9256 - it's 0.5 miles past the Observatory and campground. Park and backtrack a few dozen meters to walk around the barbed wire fence. You'll walk towards the bluff, keeping to the right until you see a trail leading up to the ridge. (The last photo shows the start of the trail.) You'll continue up the center of the ridge, finding and losing the trail as the terrain changes. There is a post marking the summit and trees for shade or stringing antennas.
For Pine Benchmark, you passed the access road a few miles back, where the road makes a sharp turn and there is a road and gate near 43.8065, -120.9416. There is an unlocked gate here and parking for a few cars (CLOSE the gate securely to keep the cattle in!). This road is passable in a high-clearance four wheel drive vehicle but not in a passenger car. It’s about 1.5 miles to a parking area below a rock bluff. A trail winds around the bluff to the left and up into the AZ. The summit is identified by a windsock. I found a nice operating position among the rocks - note there are no trees and nothing but rocks to secure an antenna mast.
There was intermittent T-Mobile coverage and LOS for 2m FM into Bend where 146.58-FM is sometimes monitored.
There is a nice campground across from the Observatory: https://www.fs.usda.gov/recarea/deschutes/recarea/?recid=39288.
