The gate with access to Boiler Ridge from near Camp 18 on Highway 26 (mp 18) is now posted "Permit Required" for all access. These permits may be expensive ($300 motorized and $75 non-motorized) and challenging to obtain (appears to sell out quickly). https://recreation.weyerhaeuser.com/Permits
Eagle Cap is a gem of the Eagle Cap Wilderness of the Wallowa Mountains of Northeast Oregon. We approached from Lostine, Oregon for a total hike of about 20 miles (32km) round trip and 4,000 feet of gain (1220m). The trail is rocky in places and often steep. We enjoyed an overnight stay in the Lakes Basin with a side trip to Eagle Cap. Only some of the 19 ten-point summits in the Wallowas have an established trail - this peak is very approachable, despite the long hike required.
Here is Eric's (VA7NX) activation story about Mount Maguire. It was a difficult session but ended with a pleasant surprise.
Crater Peak is a pleasant trail hike in Crater Lake National Park. It's been covered in a trip report by Phil-NS7P, so this should be considered a supplement. It's about 6.4 miles round trip, and although the sign at the trailhead says 765 feet of gain, that's net - the gross is more like 1,364 feet with all the ups and downs along the trail.
One of the many summits named "Lookout Mountain" in Oregon - this one is west of Sunriver and is a near drive-up with a half-mile road walk and about 200 feet of gain. It's also easy to reach by following GPS map directions.
Browns Mountain, west of Sunriver, despite being pretty close to a paved road, was a tough bushwack for Roland-K7FOP and I, as we pursued several "shortcuts." So we recommend walking about 2.4 miles on forest roads, and a final steep ascent of about 1/10 mile. Total is about 900 feet of gain. If there's a better way to get to the AZ, please write up an updated trip report.
Peak 4260 is 1.8 miles RT hike and about 600 feet gain.
Depending on how far you choose to drive, Gray Butte will be a 1.4 mile road hike (OW) with about 1200 feet gain. There's another summit that could add another two points with 1.8 miles of hiking. Although I was thinking that the road might require high clearance, a Prius drove up after me - so know your vehicle.
Pine Ridge is a steep hike of a little less than one mile (OW) and 800' vertical, close to Gray Butte-W7O/CE-180 and Grizzly Mountain-W7O/CE-135 so you might consider doing other peaks in the area. Do not confuse this "Pine Ridge" with the W7O/CE-157 "Pine Ridge" about 50 miles to the south.
Lookout Mountain is a lovely hike of about 1.75 miles (OW), close to Round Mountain-W7O/CE-045 so you might consider doing both of those peaks. Note that there are MANY Lookout Mountains - this one is east of Prineville.