We have done stories before about some of the great, huge Upstate New York State counties. This gallery looks at the ten smallest counties (by land size) in our Upstate New York Region. So take a look, and see if YOU come from one of the smallest counties in Upstate New York (by land). But in the counties of Upstate NY we see a wide variety of land sizes. Yes, these are small ones, but we also have some counties in Upstate NY that are gargantuan in size.