Well from way down here in sunny Dixie, I rode Saturday (and Sunday) Rode gravel across the mountain and 5 miles down the pavement. Started out at 17° with chill factors in single digits all day.
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And as far as bundling up, on my noggin I wore a beanie & neoprene ski facemask, which I pulled down when climbing. Light merino base layer, long sleeve jersey and a thin soft shell. Bottom was biking shorts, tights and outdoor pants on top. Wool socks and ski gloves. I had another jacket I put on during long downhills. Biggest problem is not overheating, which is easy to do when pedaling, then you sweat and get wet and THAT is what will get you. Weak links are toes. I wear bike shoes so no insulation outside of wool socks.

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I also carried lunch and a camp stove in a pannier and enjoyed a hot "backwoods mocha" to refuel. A very enjoyable day!

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