This challenge takes on three of Portland, Oregon's most iconic outdoor objectives:

1) Climbing Wy'east (Mt. Hood)--Oregon's tallest peak.  Out and back from Timberline Lodge parking lot.  ~7.3 miles, 5,200 ft.  

2) Ascending Mt. Defiance--the highest peak in the Columbia River Gorge.  Out and back on Mt. Defiance Trail from Starvation Ridge parking lot ~12.6 miles, 4,900 ft.