Trails vs. Roughin' it

Just a quick gather of opinions- do you prefer to hike on trails or do you like to use compasses, maps, and gut instincts to guide you to your destination?

I ask because my buddies and I were doing a dayhike of greylock, and as usual our mapquest directions to the trailhead led us nowhere. We asked locals for directions to any trail that would get us to the greylock summit. while on the trail, we thought it was just going to wrap around the whole mountain, so we ditched the trail and hiked up the side of the mountain and we pass no checkpoints that the map said we would. So eventually we got to the top and we could see a much grander mountain from our current summit. Turns out we misinterpreted the local's directions and thought we were on greylock, but in reality the trail would take us to greylock. Long story short, we screwed the trail and it was much more fun, though it turned out to be a disaster.