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.
Lajitas, Texas, which once elected as their mayor a goat that drank beer, has a population of 75.
Terlingua, Texas, as made famous by Jerry Jeff Walker and home of the Terlingua International Chili Cook-off, has a population of 78.
Luckenbach, Texas, as made famous by Waylon Jennings and Willie Nelson, has a population of 3.