Jason,
I live in Colo Springs. I've never done one of those tours that takes
you to the top of "the Peak" and lets you ride back down, but from what
I've seen of the road it could be lots of fun. Just believe them when
they say you'll need some insulation as you start, it's cold up there
in the summer.
If you want a pretty and fairly short ride consider the Garden of the
Gods. Don't be in a hurry, you could meet a tourist's car door in the
wrong way. There is a lot of up and down. Once there, for a challenge
ride as far up the Rampart Range road as you can. The entrance to it
is just a little north and east of the Balanced rock. It's marked.
Also consider the trail that runs along Monument creek,it's Pine creek
to the north and Fountain creek to the south, but locally if you ask
for Monument creek trail you'll get it. The whole thing is about 44
miles long from Palmer Lake north of here to Fountain in the south. A
nice day ride can be had by starting in the parking lot of Criterium
Bicycles (a nice, well stocked shop) and heading north. The sceney
become very nice quickly as you enter the Air Force academy (have ID on
your person). Once you are tired you will have a generally downhill
ride back to your car. The whole trail is good riding, but that north
section is the best as far as I'm concerned.
Tom