Hey Mike -- I just found this article on how to prepare for hills during the cold months: http://www.active.com/running/Articles/Take_Your_Treadmill_to_Hill_and_Back.htm. Good luck!
Thanks for the info. I have switched up my program in and out of the gym. I found this 2 mile loop around a business park that has a monster hill in it that should be good for training the big hill in the run. I also re-did my bike loops to incorporate more hills, but less people want to ride with me on those ones. Luckily where I live, I can train outdoors almost year round. The rain has only put a damper on a few of my workouts.
Mike--I got a lot of the same reactions! It's a bit intimidating to say the least. Yes, it would be a great idea to add some hills into your training. You are right about the cycling course: The roller coaster isn't too bad but there are some grinds. I suggest that on those grinds you pop into a low gear and just crank it out.
My friend Jesse wanted to make sure his legs were still fresh for the hilly run so even though biking is one of his strengths he forced himself to stay in a low gear and just spin out the hills.
The hills on the run weren't crazy long but some of them were reasonably steep. I was burnt out and the heat was killing me so I walked some of them. (I should have conserved energy on the bike like my friend.) I did train hills though and I feel like that helped me a lot! I had a blast on the bike portion and I didn't even mind the hills because I was prepared for them.
One thing I wish I had done more of is brick workouts--going straight from bike to run. I feel like that may have helped my performance on the run.
anyway, good luck and have fun with the hills. Once you add them to your workouts they become these mini accomplishments that fuel your rides and runs.