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Get bib shorts and use chamois cream for longer rides, it help with butt on longer rides!
I have done a few 100 miles rides alone, but I would imagine it would be easier in a group for motivation. For training i ride about 3 to 4 times a week with one of those rides being a 40 to 50 mile ride. Just take it easy and ride at a comfortable pace, it really wasnt to hard for me. And take snacks and food with you!
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