Hottest: not very hot maybe 30 celsius but with the humidity it felt like 38. So that's pretty muggy.
Coldest: -5 celsius. I really only go out on dry, snow free days
Windiest: whoa! Nearly thrown by the wind into traffic! But I have no clue how fast it was going.
Rainiest: the typical soaked to the skin rain with wind and distant thunder you get in the summertime. The coldest rain I rode thru was in November and that felt like I was getting hit with ice pellets for a few minutes.
Snowiest: my ride to work was clear with no snow in the forecast but it snowed all afternoon and intermittently thru my commute home that evening. It was about 15 cm to 30 cm on the quieter streets with lots of slush on the busier streets. This was the worst ride ever and I had to walk the last 5 blocks home because my tires were mired in snow and I didn't have the strength or balance to keep pedalling.

In order of riding preference: Hottest-Rainiest-Coldest-Windiest-Snowiest.