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.
11 points
It’s a city, it’s a really big rock, it’s a maritime port, it’s the only wild monkey population in Europe, it’s a 2½ mi2 British Overseas Territory whose status is perennially contested by Spain.