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).
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
On a quck training hike for our Switzerland Hiking / Climbing tour next July / August, I carried along my trusty ICOM - IC - V85 2M HT because it has an output of 7 Watts. Together with my old AEA "Hot Rod" telescoping vertical antenna for 2M, it seems to work very well on 2M FM. Squak Mountain, 617 Meters, 2,024 Feet elevation is an easy 4.2 miles RT hike gaining 1,274 feet to the summit. It is easily accessible from my home QTH in Bellevue, WA. Park on SR900 (Issaquah - Renton Road) or, as we did, at one of the higher trailheads on Mountainside
Peak 3534 is a near drive up in the Tillamook State Forest west of Portland off Highway 6.
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 near "drive-up" two-point summit in the Clackamas River drainage with good views. This area is likely busy in the summer but it was mostly quiet on this December day.
UPDATE March 2023: W7O/CE-213 has been retired (prominance 480 feet).
Quickly, after Old Scab I activate this plateau as well. So far the most-most easiest "hike", or more like a walk in a park. Driving only a mile further up from Old Scab trailhead I reach the top of the mountain. Here is a big open space. Park the car in the shade and start to collect this giveaway six point.