Garden of the Gods would be the place. There are some wide sidewalks that pierce the interior of the park, but I would run in the bike lanes on the road. Can't beat it for scenery. Traffic is pretty light in the mornings and evenings.
Another thought, is Cheyenne Mountain State Park. Some trails there are doable with a stroller ... but I don't know how many miles you'll get. If you find something, please share your info!
One of the best places for strollers is the Pikes Peak Greenway Trail, Colorado Springs' most popular urban trail. This is a wide, flat gravel path with some hard-surface stretches. It's popular with runners and cyclists and you'll see lots of moms and dads pushing running strollers there. You can go for miles on the Pikes Peak Greenway Trail, which connects Palmer Lake and Fountain Creek Regional Park. Here is a link to the City of Colorado Springs map ... http://www.springsgov.com/units/parksrec/maps/mppgrnwya.htm.
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