If you don't mind spending some money, Seven Falls and Cave of the Winds are kinda neat...Seven Falls is awesome at Christmas...admission is free (donations to charity are appreciated) and the Canon is lighted, falls are frozen...open after dark.
You can bike right in front of the academy on the Santa Fe Trail from Palmer Lake to Downtown Colorado Springs. Fishing near Woodland Park is not too bad. Take the Kilo bus to Monarch to ski/ride for crazy cheap. It is Colorado, most of everything involves the outdoors. Of course, if he is in the Academy, he is going to be pretty damn busy his first and second year, so he will not have to worry about it much.
I recently moved back to Colorado Springs after 2 yrs of living in Illinois. Trust me if you think Colorado Springs is bad you should try living anywhere in Illinois (except maybe Chicago). You are young, dont take offense, so I am sure bigger towns like Denver are more appealing but trust me CO is a great state to live in. You will appreciate it much more if you ever leave and get stuck in Illinois!
I think too many people underestimate the restaurants in the Springs. A nice night downtown (even in the cold) is great, mostly because it's not crazy busy anywhere and you don't normally have to wait for a seat. Then walk over to Kimbal's theater for a movie!
I'm not much for skiing so during the winter I buckle down with my friends and game! There's a pretty large gaming community for every type of game you can think of. Mostly because of the military who are some great people!
Damn, never thought this thread would go this far haha...
Anyways it was more of a question of what do most people (around my age, as in college years) do around here to stay entertained. I always thought it was kinda bad, then I moved to Fort Collins and realized that for a city approaching half a million, it's severely lacking in things to do. Although I will say the outdoor opportunities are awesome, but the whole state's like that.