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).
On 27 March Etienne (K7ATN) and I activated Silver Star mountain. The weather report called for rain with a break around mid day. We headed to the trailhead, Route: Washougal, WA to Washougal River Road (approx. 10 mi), to Skye Rd to 412th AVE to Skamania Mines Rd. Follow the signs to silver star. We reached the TH at about 0840 and started up the trail. At about 1/8 of a mile the trail splits, take the right split. We found out the hard way and got about 1/4 mile down the trail before I checked the map and realized we were on the wrong trail.
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
A very long day to get ten points - the usual for the Northwest.
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.
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.