This doesn't win the contest, but some years ago on the way back from an east coast trip. Problem was is that it was a spur of the moment thing in October when the weather seemed okay. Well, it was, mostly. I was not prepared for when it started snowing in New Brunswick and concerned looking people were asking me questions in French. I put on my rain suit just for an extra layer, but it didn't help much (seemed to be a strong headwind the whole way home) and it whipped around in the wind. Started yelling in my helmet for warmth, which seemed to help more than the rain suit. The Quebec stretch is a blur, all I remember is that it was cold, and windy, and miserable