In Doug Lorain's Afoot & Afield book he describes a hike to Wind Lake, which is kind of behind Skibowl north of Tom, Dick, and Harry Mountain. I decided to go check it out. 
The Skibowl Adventure Park was already buzzing with activity when I got there at 10am. Following Lorain's directions I started out on Lake Road to Low Road to High Road to Skyline Road, weaving my way up the hill.
Hiking under the Multorpor chair lift, where the parade of silent red seats marching up the hill looked kinda cool:
I started getting nice views of Mt. Hood around that point:
I reached the historic warming hut, which was built by the CCC in 1936:
Staff were setting up for a wedding later in the day. This would be a beautiful spot to get married, but it's quite exposed. It was a pretty breezy afternoon and the various drapes and fabrics were waving around.
At this point Lorain suggests taking the Cannonball Trail up instead of the road, but I do NOT recommend this. The trail is used by mountain bikes and you don't want to get plowed down. Plus it is very very steep. Stick to the road.
Up on the ridge before reaching the top of the Upper Bowl chairlift there is a well-signed trail heading off to Wind Lake. This trail is quite rocky and I didn't see any tire tracks, so I don't know how well-used it is by mountain bikers. This trail goes downhill from the road, but fortunately there wasn't much elevation loss. When I reached Wind Lake it was peaceful and devoid of people.
While munching my snacks I was perusing the map and I discovered that Wind Lake actually sits just inside the boundary of the Salmon-Hucklberry Wilderness. Interesting.
On the way out I passed a large group (15-20) of hikers that looked like they were on some kind of guided outing. I wondered if that was something offered by Skibowl, but I don't see anything on their website.
On the way down I had a bird's eye view of the warming hut and the wedding area that was now done being set up.
I could also see some of the buildings of Government Camp:
Mount Hood, looking pretty naked this late in the summer:
The warming hut again:
At the bottom I stopped on the footbridge over the alpine slide and watched for a few minutes. That looks like A LOT of fun! I'll have to do that sometime.
Parting shot:
If you go here it would be a good idea to have a copy of Skibowl's summer trail map with you. The network of roads and trails can be confusing, especially since none of them show up on a GPS or the regular MHNF maps. Most of this hike is road walking which is not fun, but the lake is a nice spot away from the crowds (well, unless you happen to be there when a guided group arrives!).
