So I have done this path in both directions several times as I live near by. It definitely depends on the day, but I think I like going up from the Breck side better. It is longer (about 11 miles up) but the feel is very European from this side. Plenty of switch backs and a wicked view down into the Valley. From the Fairplay side it is much shorter, but it is also pretty steep. Did it this when a groups of us did the triangle of Boreas, Red Hill and Hoosier Passes for a great loop and 3 Passes Stamped!