This is a straightforward drive-up activation about an hour south of Bend with great views. Paulina Peak and North Paulina Peak are both in the Newberry National Volcanic Monument - you might consider a double activation of these peaks and an overnight stay in one of the campgrounds.
On summer weekends the summit may be quite busy as the parking lot is large. However, for this early fall activation there were only one or two cars at a time up there. The road is about four miles of gravel with some washboard that can be driven by any passenger vehicle.
There is an admission charge or Northwest Forest Pass required. Newberry Crater is just over one hour total travel time from Bend. Head south on Highway 97 for 23 miles and then go east on Paulina Lake Road about 13 miles. There are campgrounds around Paulina and East Lakes and along Paulina Lake Road.
About a quarter mile past the Visitor Center there is a clearly marked right turn for Paulina Peak. For those that would like to hike some of the route, there is a wide spot in the road about 3.3 miles up where the Paulina Peak Trail crosses the road. The trail elevation gain is about 400 feet from here over about six tenths of a mile. (I elected to hike down the trail 100 feet of elevation and then back up.) At the summit there are a number of places to set up to operate to be out of the way of the tourists enjoying the scenery - although vertical antennas may be a bit easier to set up than long wires. You might be prepared to answer questions about your radiosport from a few inquisitive folks.
Note that there were decent APRS digi echos from the summit but there might not be coverage from the trail.