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Roadtrip November 17th, Chicago to Colorado.. through WI, MN, SD, WY??

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Hey guys! So I don't have any specifics yet, but I'm working on planning a roadtrip from Ohio to Colorado. We'd stay with friends in Chicago until Tuesday the 17th, then we'd have about 6 days to get to Colorado. Any suggestions? I've already been through Nebraska and Iowa so was thinking maybe just a bit north... hit up Madison then through southern MN, try to hit the Badlands, Mt. Rushmore, etc. in SD, then probably head south in WY just across the border and down through Fort Collins and Boulder/Denver.

About us, it'll be me and my boyfriend. We're 22 and 21, enjoy hiking and picturesque scenery (but maybe not too much hiking considering it'll be the end of November?), smaller towns and cities, national parks, microbreweries, anything interesting. Neither of us has been to any of these states (besides Colorado). Any ideas on where to go and what to do, what the weather will be like, how long we should stay in certain places, etc. would be really helpful. Also, if anyone has ideas that I haven't thought of yet, go for it! Maybe we should rush through all those places and head to Montana as well? Or maybe we should forget everything in the north and head south through New Mexico?? I've done the trip through Oklahoma, northern Texas, and New Mexico, but wouldn't be against doing it again but slightly different. Any and all ideas would be greatly appreciated, thanks!!!!

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