User blog comment:Thedoucheinthenorth/Should a city-sized Winterhold have been in Skyrim?/@comment-1840877-20121111093301

Like DarthOrc said below, you'd never get a thriving city in Winterhold simply because it's such a desolate place. The only settlement there, other than the city of Winterhold itself, is one small iron mine. Nothing can grow there, and their jail is a hole dug into the ice. Winterhold is simply too inhospitable to have even a remote chance of a thriving community growing there.