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We have settled on our initial speed skate route, and we'll be doing the first official speed skate this Thursday, 5/27/2010.
Headlights ARE recommended (though not required). We also strongly recommend you wear a bucket and pads, and you should have some sort of bright red, flashing rear marker too.
Generally speaking the streets we're skating on have very little traffic, but you will encounter traffic, hills, railroad crossings, and the occassional patch of bad pavement.