Machka 

I lived in Winnipeg for 13 years, and cycled year round for at least the last half of those years. Several Winnipeg cyclists do.

I did a Century-A-Month challenge in Winnipeg (in 2003), and two Century-A-Month challenges in Red Deer (in 2005 and 2006). 100 miles in one particular day, in each month of the year ... even if those months are November, December, January, and February in some very chilly winter weather.