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Spearfish, SD makes a good base for the area. Other folks have covered most of the local venues and sights. As far as the trip. Give yourself time to enjoy it along the way without making every day an Iron Butt run. Don't ask how I know.
if you plan on slabbing it via I-90 then the best advise i can give you is to avoid Chicago at all costs. a couple of years ago i went from West. Co. NY to the national in Gillette WY and found getting through Chicago was the worst part of the trip.
I wouldn't say it's "barren" ..you are in the heart of the Plains where grass is prominent and the wind blows constant and you only see willow and cotton trees lining the rivers and streams. There are stops along the way..may I suggest stopping at Wall Drug(bordering the Bad Lands) as one of your destination stops(equivalent to South of the Border on I-95).Another question; Can anyone tell me if the stretch of I90 between Sioux Falls to Rapid City is very barren? Lacking gas, food, stops etc. Glad to hear input
Another question; Can anyone tell me if the stretch of I90 between Sioux Falls to Rapid City is very barren? Lacking gas, food, stops etc. Glad to hear input