I've led the trip several times for Adventure Cycling westbound. It's always good to have an extra meal packed away, but you may never have to carry it... aside from buying supplies early in the day when your camp may be out of town. Examples would be Breaks Interstate Park, VA and Rosedale, VA. If you arrive late you might find little in Hartsel, CO and Jeffrey City, WY. If things are closed in Wisdom, MT go to the bar. Looking at everywhere else on my itineraries there is at least a convenience store if you don't roll in too late.
Rockies? If you're headed to Chicago I assume means that you're travelling east. For westbound riders they don't seem too bad after the steep, hot & humid climbs of the Appalachians and Ozarks. The climbs in the Rockies are longer but more moderately graded. The toughest for me was Currant Creek Pass between Royal Gorge and Hartsel, CO. A long, dry climb with thin air that you haven't acclimated to yet if you're riding west.
Thunderstorms? Two of three trips... not a major problem. One trip, though, we were cycling through tornado alley in KY, MO, and KS during an active season. Every afternoon for a few weeks the sky would turn ominously green and we'd have to decide if it was safe to continue through exposed, open prairie or stop short of our planned itinerary that day. There was lots of waiting out storms on porches of kind locals and lots of stopping early. In KY we had a storm violent enough to damage buildings, bring down power lines and to separate our group for a day. In Larned, KS several tents blew down at the City Park in the middle of the night. The occupants had to seek shelter at a covered picnic pavillion. Yes, t-storms can be a problem.
Dogs in KY? YES! At least one group member got bitten. Not a major problem though. Slow down or stop and the challenge is gone for them!
Water? I agree with Sean. Not a major problem. Places you might run dry? Westbound from KS to Pueblo, CO. Westbound again from Pueblo to Canon City. Also between Rawlins, Jeffrey City, Lander, and Dubois, WY. Carry plenty around Brownlee Dam in ID and also through eastern OR between Baker City and Mitchell.
This message was edited by BobG on 6-12-04 @ 7:43 AM