Challenge Hill, Philip S. Miller Park in Castle Rock

Distance: 0.15-mile climb (200 steps) plus 0.6-mile trail
Difficulty: Moderate
Cost: Free

Ignore the runners zooming past you and focus on putting one foot in front of the other as you climb the 200 wooden steps to the top of Challenge Hill in this expansive urban park. If you need an excuse for a breather, stop for a photo-op at one of the markers that appear every 10 steps. After congratulating yourself for reaching the top, take in the city views and try to make out the friends you left behind on the soccer pitch or 2.5-acre playground. (With so much room to play, kids may prefer to test their mettle in the American Ninja Warrior–esque adventure park, which includes a warped wall.) You have two options to return to the parking lot: Circle down via a quick and easy dirt path or, in non-COVID-19 times, walk back the way you came (currently, you’re only permitted to travel up the hill).

Who Will Love This Trail: Stairclimber fiends; competitive sorts

In Comparison: Something to think about while you’re climbing: The famed Manitou Incline in Manitou Springs (which currently requires a free reservation to visit) rises 2,000 feet over about a mile. And has 2,744 steps.

Daliah Singer
Daliah Singer
Daliah Singer is an award-winning writer and editor based in Denver. You can find more of her work at