Jeans and boots? How many miles will you be riding in jeans? Anything longer than 5 miles and I need padded cycling shorts. Will the temps still be warm in late September? If I were you I'd rethink the plan.
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The Lord is merciful and gracious, slow to anger and abounding in steadfast love. - Psalm 103:8
I am a cyclist. I am not the fastest or the fittest. But I will get to where I'm going with a smile on my face.