There's a nice organized ride near here next weekend. It's got an easy 20 mile route or a 60 mile route. The problem is that the 60 mile route has about 38 miles that are on a dirt road. It used to be a regular paved road, but it hasn't been maintained. I'll be on a road bike with 700 x 23c tires at 120 psi.
I really am a smooth pavement prima donna, but I'd like to take the longer route.