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Medora, North Dakota - Nearest town is 3.9 miles away, nearest city of over 50,000 is 130 miles away. The towns near it are all under a 1,000, but it's under a hundred itself.
Looking through with less concern on the density of a county, though these might also be in some of the most sparsely populated counties, I find the following to look pretty isolated.
Colby, Kansas - I believe it was mentioned on an episode of "My Name is Earl." Anyway there are some towns close to it, but they all look to be smaller than it. McCook, Nebraska might be the closest town to Colby to have over 6,000 people and it looks to be about 79 miles away from what I found. (Although one source seemed to put places in Colby as around 56 miles from a McCook airport or something) For Colby the closest city of over 50,000 is 201.4 miles away.
Mullen, Nebraska - A much smaller town than Colby at just 481 people, but it looks like none of the nearby towns are even that "big." North Platte might be the nearest town of over 10,000 and it looks be 72 miles away. The nearest city of over 50,000 is Rapid City, South Dakota, which is 178.7 miles away.
Crosby, North Dakota - A town of around 900. The other towns in its county have under 200 people and the map doesn't seem to show a city of over 2,000 to be too close. (In ND all incorporated places are cities) Williston looks to be the closest cities to have over 6,000 people. Williston is 68 miles from Crosby. The nearest city of over 50,000 is Bismarck, which is 186.3 miles away.
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