Having experienced both, we vote for Ithaca, NY’s Cascadilla Park Road as the definitely better winding street. Here is the satellite view of Cascadlilla From Google:
Let us count the ways – much better thrill factor. Cascadilla is two way traffic and you are also likely to meet pedestrians hiking to or from Cornell. Cascadilla is much better visually – you wind 270 degrees around houses, potentially coming within inches around the impossible corners. And if you are driving up Cascadilla (our recommended direction) you can sneak nano-glances into the Cascadilla Gorge and its stream bed bottom a hundred feet below while trying teasing your vehicle to stay on the pavement. Finally Cascadilla is longer and rises far more than Lombard.
Assuming you are still allowed the next time you are in Upstate NY, driving up Casadilla Park is one of the the “Top 100″ things to do in the Finger Lakes Region. Help generate the buzz East tops West – again!