My auto mechanic is right at 9 miles from my house so I was going to ride the bike to pick up my wife's car. Between the two is this God awful hill. I'm still trying to get used to the clip on shoes and toward the top of the hill I'm standing grinding it with everything I had and I realize I'm running out of strength and so much so that I'm pretty sure I can't even get my shoes unclipped so it's hit the peak of the hill or crash. I did make it up barely but it was gut wrenching. I would not normally choose that road just because of that hill.
You talk of doing 40 miles. Are these routes in big repeated circles or are you running one big 40 mile loop?