Tom Dick and Harry Mountain is perfect for a nice, easy day tour. This area is just to the west of Skibowl, and will have snow conditions that are very similar to the recreation area. Most of the skiing area is north-facing, so the snow suffers less melting and re-freezing than other areas.
Because parking at the trailhead just off of US Highway 26 causes traffic hazards, parking for this trail (and for Mirror Lake) is in the Skibowl West parking lot. While undoubtedly a safer arrangement, this means that the first mile of the route requires a walk west along the highway. Just follow the tracks on the south side of the highway that lead from the Skibowl West parking lot. After 0.8 miles along the road, the official trail begins at the Mirror Lake trailhead. Cross the bridge over Camp Creek and follow the trail up the hillside.
This trail sees heavy use from snowshoers and hikers, and it is easy to follow in most conditions. After 2 miles of moderate switchback climbing you will come to a junction: take the left turn to go directly to Mirror Lake, or turn right to follow the Wind Creek Trail to the top of Tom Dick and Harry Mountain. If you are patient and trying to conserve energy, stick with the easy trail and refrain from cutting a steeper trail to the top. When snow conditions are right, you'll get some very nice turns along with excellent views of Mount Hood. There are many available descents, ranging from moderate bowls to massive cliff bands. Pick your poison, but remember to check avalanche conditions and to practice safe avalanche awareness at all times.
For an alternate route on your return, traverse east and cut below the large rock face. This route puts you into the Skibowl ski area boundary where you can easily ski straight back to the parking lot, avoiding the crowded trail from Mirror Lake and the noisy mile along the highway.
Winter backcountry adventures can be dangerous outdoor activities that pose significant risks as conditions affecting safety (i.e. weather, snowpack stability, avalanche hazard) are constantly changing. Prior to engaging in these activities each individual should get the proper training to make safe decisions and be equipped to use avalanche safety resources and tools. Please visit our Backcountry Skiing and Avalanche Safety post to learn more.