trevor, a double is the only way to go, only old guys ride triples, lol. actually since i've never done it i couldnt tell you what would be better or worse, but if it happens, i plan to do it with a double, on my roadbike. and if it matters, for the present time being, i have my car in the city, with a rack for holding 3 bikes, plus a 4th in the trunk, and room for 4-5 people in the car (tight fit). so if anyone is really serious about the wachusett climb, it would be awesome to try. i would first have to swap out my front fork on my bike though, since its crooked and has a wicked nasty speed wobble (crashing at 50mph is not fun, as i learned the last time i tried it)