In the United States, I'd probably name Oregon City, the famous end of the Oregon Trail and the first city founded west of the Rocky Mountains during the pioneer era. Its population is only 37,000.

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[โ€“] 47 points 2 years ago (2 children)

For the US, I'd say a pretty strong contender is Woodstock, NY, with a population of around 6,000, and of course famous for the music festival of the same name (even though the actual festival was something like 60 miles away in Bethel)

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