How should I train for a hilly ride while living in a flat country?
Intervals. Lots of intervals. I had a similar problem when training for the Seattle-To-Vancouver ride while living in southern Michigan. We have hills up north and I took a few trips there before the ride, but it really wasn't enough to reduce the suck. This year, I've taken to doing tons of intervals with a regimented training program. In order to keep myself honest, I've been using my bike in a trainer with trainerroad. The measurable progress is rewarding and knowing when I am slacking off is incredibly motivating.