Somewhere warm & suburban. There are some guys on here who commute year round in Chicago, Cleveland, Buffalo, etc, but in reality, winter & snow make it a lot harder to commute. not impossible, but they do add some complexity. Suburban areas are nice for riding, as you are close enough to the city to still have good services & ample shopping/dining/ recreation opportunities and suburbs generally offer more side streets than rural areas where a lot of the riding is on high speed streets. At the same time, you are away from the really nutty rush hour traffic and congestion of the big cities. If I could live anywhere in the US based on where I felt I could ride the most, I think it would be suburban San Diego. Not sure about the teaching job market or cost of living (although CA in general seems to be high), but that is just such a beautiful place all year round.