last night, we found ourselves one block from the infamous Lombard Street, and Randall mentioned that he'd never driven down it before. Naturally we made up for that and drove down it right then (it was past 11 and the line was gone). Once we were done, Randall told me that while Lombard was more picturesque, he was positive that Vermont felt windier. I tried to make him take me then so we could see, but he said we should wait until the morning, especially because he didn't think all this windiness went with all the wine i had been drinking.
So we went today, and according to wikipedia (which, as you know, is never debatable) Vermont is indeed more "crooked." You can see for yourself: