There are at least four trails that approach the summit of Big Huckleberry Mountain - we choose the Pacific Crest Trail from the south for about 8.6 miles round trip and 1400 feet of net elevation gain (1900 total).
From Portland, take I-84 to Cascade Locks and cross the river for two dollars (2019 price).
Here's a six point summit to tackle on a nice summer day - we tried it with lots of snow and found a blizzard at the top in mid-April. The trail is on a road of about 7 miles round trip and about 1800 feet of gain.
From Portland, take I-84 to Cascade Locks and cross the river on the Bridge of the Gods (toll).
I did this summit on 26 March as it was close to where I was staying. It poured rain on me the whole time but I came out with 14 quick contacts including a S2S with Etienne K7ATN on 146.52. I drove up the road and until my truck would not make it any further (4WD) and then hiked up the rest of the way. If you look at my everytrail tracks the "GO" marker is where the dirt road starts and the "END" marker is where I parked the truck. You could drive further then this if it was a dry day or if you had a jeep or 4 wheeler.
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.