Having a tailwind is fun manly because the speeds that are obtained is crazy. I enjoy watching the bike races when they have a cross wind as the bunches tend to break up and those out in the front pull away. It is a skill riding in the wind, but more so on a single gear bike which sounds really hard going.
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it is fun but not if you have the wind at your back at the start and have to ride back in the opposite direction to get home after you are already tired. That happened to me once and I will not make that mistake again. I suppose the good thing about it was that I got a much more intense workout than I had planned on getting and I had no choice but to power through!
Yes I have had that before and it is hard work pedaling into the wind and would not be ideal finishing a ride with a head wind.