Never in the rain, but I did have a ride when I was a total novice to cold-weather riding that was awful.

My ride partner and I were trying to squeeze in one more ride in the fall and the day was suppose to be sunny and about 55 degrees. We set out on a long ride in the middle of nowhere about 4 hours before it got dark, assuming we would be riding as fast as we always do and could get the ride done well before it got dark.

Well, the sun disappeared behind clouds, the wind kicked up, the temp dropped to 40 and there we were with no gloves, just shorts on, no lights, not enough food, etc. about halfway through the ride. Then her rear brake locks up and neither of us knew how to disengage it using the quick release (didn't even know brakes HAD a quick release at that point). So we had to slow way down for that dragging brake and it started getting dark.

The only piece of luck was the plastic grocery bags I had in my trunk bag that we fashioned into gloves. This was on a limestone rails-to-trails path so there were no lights anywhere and it was pitch black by the time we got back to the parking lot.

I'm laughing at myself now as I write this - we were so stupid!! We stopped for a Starbucks to warm up on the way home and felt very macho about surviving that day!