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. A Forest Pass is required from May 15 to October 1 - a SnoPark is required November 1 to April 30.
The trail starts as the very popular Mirror Lake Trail - there will be plenty of people on this trail during weekends with nice weather (trailhead info here - access now from Skibowl parking lot). Fewer go beyond Mirror Lake to the steep ridge above and hardly anyone besides a SOTA devotee will venture to the true summit on the eastern part of the ridge.
From Mirror Lake there will be an unsigned trail leading west away from the lake - this is non-intuitive perhaps, but the trail to the summit leads mostly west, away from the summit, about 1.5 miles to gain the ridge - then there's a sharp left turn at a large boulder cairn that you may not recognize as such in winter - see the photo below. From here it's another mile or so along the ridge top to the summit. A good map and a GPS may give you some comfort that you are on the right track to the summit. Following the ridgeline itself will give you good views but may require taking snowshoes on and off or clambering across large dimension scree. Traversing along the slightly less steep southern slopes is much easier. Following the trail in summer is a fun challenge.
When you seem to "arrive" at the summit where everyone else stops to admire the view of Mt. Hood, you are still about 0.6 miles from the summit and not yet in the AZ. There are several high points that may seem to be in the activation zone but there's a saddle between them and the true summit - finding the top of the SkiBowl road and the Warning signs to ski within bounds will indicate that you've arrived.
You'll see that the highest SkiBowl lift is not far below the summit and in fact, there's a road up here for lift service and as a ski trail. You may be tempted to take the ski runs down to the parking lot but these double black diamond ski runs are not recommended, especially on snowshoes (I've tried it - once).
Other hiking guide information for Tom, Dick and Harry: http://www.backpacker.com/destinations/hikes/7739
http://www.portlandhikersfieldguide.org/wiki/Tom_Dick_and_Harry_Mountain_Hike
