Waldo Canyon is  a very popular trail off highway 24 near Colorado Springs.  I hiked this trail in February with my dog Tripp.

The trailhead is directly off Highway 24.  After leaving the trail head the trail climbs steeply up and away from 24.  It only takes 20 minutes or so to get out of sight / earshot of the highway.

Here is the Trail head in google maps

GPS Track of the hike

More Detailed information about this hike can be found at http://www.localhikes.com/Hikes/WaldoCanyonLoop_1720.asp 

Here are some nice pictures of the trip 

The hike is a nice gradual climb.  You follow a lollipop shaped trail up into the canyon.  In the winter the west side of the canyon can have lots of ice.  I would recommend having microspikes or some other traction device to do this hike in winter.  Near the top of the canyon you are treated to really great views of pikes peak. 

There is a back country campsite near where the loop starts.  It looks decent but is sure to see tons of daytime traffic as it is directly on the trail.