Yes, I live in Kalamazoo, but this is my first year riding, so I don't know how late into the year I will ride. I am hoping to make it at least until Thanksgiving, but we will see. I have a feeling that I will be stopped by cold before I am stopped by snow.
You might want to post the same topic on the Michigan forum, there are a lot of helpful Michiganders there.
They are cool with recommendations about gear suited to Michigan's weather and trails. Also they are a good source for recommending trails based upon ability and preferred riding style. Also check out:
What do you wear to keep your ears warm? I can deal with cold in pretty much all other places, but cold ears just ache.
Also, as for the "where to ride" question. I was thinking about checking out a few local trails and seeing if others were riding there. If it looks like it has been taken over by x-country skiers, I will probably leave them alone because I don't want to hack it up for them if nobody else is biking.
I just used an insulated head band like I'd use for X-country skiing. I made room in the helmet by removing the sweat band from the front of the helmet. I also used a bandana inside the helment to reduce the breeze across my scalp.
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