Pine Mountain (W7/CN-058) and Pine Benchmark (W7/CN-068) are close enough that one could easily do both summits in a day. There's a bit of bushwacking and route finding to be done, but at most you are walking less than four miles to do both of these summits. 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 four miles (?) look for a left turn for NF-100 as shown on Google Maps. It might be numbered differently there (250?) but it is the righthand of two roads heading towards the summit. NF-100 also appears to be suitable for any vehicle and will take you to within a quarter mile of the summit. Find a good place to park and hike up the steep hill to the open summit. There are pine trees for stringing antennas and a rock shelter down off the top if you find yourself there on a not so nice day.

For Pine Benchmark, continue up the road another few miles until the road makes a sharp left turn. Here there is a road that can been seen on Google Earth but not on Google Maps. I believe the sign said 350. There is an unlocked gate here and parking for a few cars. 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 into the AZ. The summit is identified by a windsock. I found an operating position among the rocks near a steel pole.

There is a nice campground across from the Observatory: https://www.fs.usda.gov/recarea/deschutes/recarea/?recid=39288.