This is a fine hike that many should try at some point - it's 4.4 RT miles and 800 feet of gain for the 'short' version described here, with a summit pinnacle that makes for a fun scramble if you feel the need to get to the tippy top.
As part of our annual summer trips Paula, N6VGW and myself (WA6ARA) try to go different routes and have fun along the way. As part of our 2014 excursion we stopped by Crater Lake in Oregon for a few days. While there we did a a couple of Summits On The Air, or SOTAs. These were Wizard Island and Mt Scott. While Mt Scott has been activated often, Wizard Island had never been activated. Wizard Island, is in the middle of Crater Lake so you can’t walk there, it is a boat trip and reservations are usually needed.
Silver Star is a classic hike in SW Washington that should be on everyone's list to do at least once.
Bull of the Woods is a pleasant and popular hike south of Estacada of about 6.5 miles and 1300 feet of gain. There's an unused (but locked) fire lookout at the summit, giving you a chance to be out of the sun (or rain) to activate by standing under the structure.
Here's a near drive-up south of Estacada with a hike as short as a quarter mile and 200 feet of gain.
UPDATE 2021 - Mount Lowe may have been damaged in the September 2020 fires. Check for access.
Rock Butte is a short bushwhack with no views or other redeeming qualities in the Activation Zone. It's just past Timothy Lake east of Mount Hood.
Wards Butte is near Cottage Grove, Oregon and can be accessed from the south by I-5 exit 170 and from the north by exit 174. (Not to be confused with Ward Butte-W7O/CC-082.)
Mount Pisgah is a 'near' urban summit just east of Eugene. It is known as Mount Pisgah Arboretum and as the Howard Burford Recreation Area. It's a short 1.5 miles, but steep with 1050 feet of elevation gain from the parking lot to the summit. It features some of the last remaining oak savanna that once dominated the Willamette Valley and the summit has good views.
Here's a pleasant and easy pavement drive-up activation just east of Madras in Central Oregon. You might consider it as you travel between Bend and Portland sometime. There are nice views from the top, good parking, and trees and sagebrush to support most antennas.