County: Fairfield County
Size: 22.5 square mile
History: Does anyone really care about the history of New Canaan? No, we care about the lengthy list of celebrities that call it home. But here’s our half-hearted attempt at pretending we care. In 1731 the Parish of Canaan was given the right to have a church, but the people who lived there were technically still citizens of Stamford or Norwalk–which would no doubt enrage the present residents of this ridiculous town.
After the Revolutionary War, New Canaan became a hub of shoe-making activity, which is pretty funny considering it is now a hub of shoe-buying activity. It wasn’t until 1868 that wealthy New Yorkers finally discovered the town and started building summer homes there, which brings us pretty much to present day where New Canaan serves as a place for rich NYC businessmen to keep their families sequestered from their mistresses in the city.
Something Weird: For reasons I don’t really understand, New Canaan was a hub of modern architecture activity from the 1940s-1960. A bunch of Harvard students and teachers were responsible for this–which Yale should be ashamed of–and they built about 80 modern homes in the town…because nothing says New England charm like a glass box.
We assume raging a*holes and New Canaan residents Ann Coulter and Glen Beck live in some of these modern monstrosities. We think it would be funny if they live next door to Norman Cousins, a peace activist. David Letterman, Martin Mull, Katherine Heigl, Christopher Lloyd, Paul Simon, and the hilarious Brian Williams all call (or have called) New Canaan home.