Hill City should be as good as any for late season. Not much for restaurants there, a Mexican place downtown and another on the northeast side that has gone by various names. Be sure to visit Nicodemus, a black settlement begun just after the Civil War and still the same today.
If you have snow or rain, dirt roads around there bog down quickly. Some drain but others have no bottom and the same length of road can have both.
Look for the heaviest cover and pockets that you can find this late. Good luck.
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