Summary - Gifford Peak is approached via good trails and a steepish cross country bushwhack. From the Thomas Lake trailhead, hike both East Crater and Gifford Peak as a ten mile outing with 2500 feet of gain. From Carson, WA take Wind River Highway up and all but the last bit of the two hour drive (from Portland) is on paved road. A NW Discover Pass is required and this is a popular area, so the parking will be tight on weekends. 2M contacts into Portland, Hood River and Mosier are possible and setting up an HF wire is easy. This is a "choose your adventure" ascent. You should be comfortable with a compass or have reliable GPS for navigation. This is definitely not a bushwhack to try in poor weather.
TL;DR - Indian Heaven is a beautiful (and popular) wilderness area west of Mount Adams with a chain of peaks (Red, Gifford, Lemei, East Crater, Bird, and Sawtooth) and the PCT running through it. The best time to hike is in the late summer or early fall, after the bugs are gone, while the meadow/marshes are mostly dry, and before the rain and snow begin. The ambitious could probably summit all six peaks in two or three very long days. My outing was somewhat less demanding: East Crater and Gifford Peak via a ten mile loop that included two stiff bushwhacks. While both summits are near good trails, this is a "choose your adventure" outing: the summit climbs are cross country in complicated terrain, so map and compass skills are a must, as is comfort negotiating thick brush, snags, and the like.
After consulting with Tyler ND7Y, I took the Wind River Highway up to NF6507 to NF65. All but the last couple of miles are on paved road and 2WD easy. The drive from Portland is roughly two hours. A NW Discover Pass is required to park. This is a popular trailhead. I arrived at 700AM on a Saturday to claim the last spot.
From the lot, take Thomas Lake Trail #111 roughlly 2 miles. Here a trail heads east toward East Crater while the Thomas Lake trail turns south toward Gifford Peak. If you are doing the loop, I recommend doing East Crater first. If not, turn south here. Follow this through older forest, alpine meadowns and around several lakes until you reach Umtux Lake at (45.99005, -121.80301). Plot a route up around the lakes and stay on the west side of the ridge, working your way through bands of brush, new trees and snags. At the top, behind the rocky nose of the ridge, find a place to traverse to the open terrain on east side and walk to the summit.
It is easy to set up a wire here and I made four contacts on two meters within ten minutes of turning on my HT. I had no problem spotting with ATT cell service, so I didn't turn on APRS. The summit is open and has great views in three directions. When you are done, follow the same route back down to the Thomas Lake trail and go from there.
While the bushwhack requires, well, a lot of bush whacking, it is relatively straightforward if you are comfortable working with a map and compass. The views are great and East Crater is a good hill to hike from the same trailhead.
Info on East Crater can be found here.