Check out my blog at http://kf7pxt.blogspot.com/2014/03/larch-mountain-w7wlc-103-sota.html for additional information.
Here is my everytrail post with downloadable GPX tracks - http://www.everytrail.com/view_trip.php?trip_id=2713566
Tom, Dick & Harry Mountain is a nice late season snowshoe near Mount Hood. It's about 4 miles one-way and 1850 feet of gain to bag this four-point summit with iconic views of Mount Hood. It's a bit of work with some route-finding on snowshoes, but hopefully this trip report will help you get there.
Peak 3534 is a near drive up in the Tillamook State Forest west of Portland off Highway 6.
These eleven miles (RT) seem much farther when you are on snowshoes - take that into account if you should decide to try this winter activation.
Along Highway 22 between Salem and Detroit there is a near drive-up summit. In 2013 the road was passable (with some care) in a passenger car. (It may be a bit overgrown now.) This summit could be a back up plan when nearby Rocky Top can't be accessed due to snow.
Here is an urban 'pavement' activation - the closest one to downtown Portland. The summit proper for Cornell Mountain is on private property with the Activation Zone accessible from a neighborhood street with very limited shoulders.
A fairly short snowshoe near Mt. Hood gets you two points - in the summer this activation may be a bit more challenging in the bushwack.
UPDATE March 2023: W7O/CE-213 has been retired (prominance 480 feet).
This yet unnamed peak deserves a good name as it's a very worthwhile activation. It's a bit out of the way but very quiet compared to nearby Lookout Mountain and the views on a clear day of Mount Hood are excellent. These are directions from the NORTH - this road is suitable for HIGH CLEARANCE vehicles that you don't much care about.
Another highly recommended hike and activation - this one in the Clackamas River drainage.