The Whipple Trail System begins right out of the river park in downtown Buena Vista. Begin by taking the bridge across the river, and then start climbing!
There are 3 different routes to the top: the Wipple Trail, North Whipple, and South Loop. Some are a bit steeper and rockier than others, but most of the climbs are quite manageable.
Once you finish the climb and hit the Midland Trail/old railroad grade, be sure to grab the Broken Boyfriend trail on the other side. The longest trail in this trail system, it climbs and dips along through the scrub pines and up and over rocks on dry sandy, soil. Be sure to stop every now and then when the trees open up and enjoy the fantastic views of Buena Vista and the Collegiate Peaks!
Next, either take the old railroad grade up/east-southeast to the Midland Hills trails, or grab one of the other trails in the Whipple trail system to drop back down to the Arkansas River.