As for attire, posting what you have picked out would be helpful.
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But the route up the GAP trail and across is new to me, so I'm thinking that's the way I would go.
I have found that working with the bike shop inside of the REI store to be just like working with any other bicycle shop. Just call the local REI store number and ask for the bicycle service person. I don't think you will be overwhelmed at all.
......we were both disappointed in the dinner at the Syracuse Zoo.This opens so many opportunities for wisecracks I don't know where to begin.....
(Those Trans Am alternatives look cool, btw, thanks.)
On the PDF overview map I found a new route called the Chicago New York City route.