I took an AWESOME couple of hour ride through Westchester (a county just north of New York City) this past Saturday and I just wanted to share my experiences with you guys.
First, I was little hesitant as the temperatue was like 25-27F and I have never ridden in a freezing weather but it was so sunny and nice otherwise. I always wondered how you guys up there in Minnesota, or Canada manage to ride so late in the season...
I was VERY surprised that if you have the right gear, the experience is really very pleasant and the seemingly harsh weather is not a problem at all. It reminded me in many ways of skiing - cruising up and down through a hilly, snow covered country.
A few things that I learned - after about 30 mins the gloves I had felt cold in the figertips. I really need to try the trick that some guys in the forum suggested -- thin gloves inside the bigger ones.
Also, I wear a open face helmet with a face shield. The cold air was hitting my chin at the bottom on the shield. I think I would have been much more comfortable with a full-face helmet (I know, it's viewed upon as un-cool on a cruiser, although I am still not sure why...)
A serious thing to watch out for is the ICE -- they were ice patches especially toward the edge of the road - although not wet, as it was freezing. I ran over a few (no braking, no turning, just like coasting on a bicycle). It was a bit scary at times at did not slide a bit, but still I think this is nothing to be underestimated.
If the weather is nice I will do it again next weekend. I just hope that the roads are dry. I really do not want to get the salty spray all over the engine, radiator and everywhere. I do not even have the hose attached by the garage anymore because of the frost!