The Cherry Creek Trail is one of the better urban greenway systems in the western US, running about forty miles from the South Platte confluence southeast out into Aurora. The central five-mile stretch through downtown and the Cherry Creek shopping district is lined with mature cottonwoods, mostly on the north bank, where the city planted them in the 1960s as part of the original trail build. The cottonwoods on the south bank are younger and patchier; the canopy there is more like 60% coverage to the north’s 90%.
The geometry trick is that the cottonwood cover on the north bank shades the south bank trail in the morning, when the sun is east-southeast, and shades the north bank trail in the afternoon, when the sun is west-southwest. So the right side to walk on flips around 1 PM. The picks below are split between morning routes (south-bank) and afternoon routes (north-bank). Stay Cool will swap you between them automatically if you save a midday route.