Size: 28.7 sq mi
History: While South Windsor was not officially incorporated until 1845, its roots go way back to 1659 when Thomas Brunham bought some land from the Podunk Indians. (Terms of the deal were not released but it’s safe to assume the Podunks got jobbed.) Way back then, agriculture was naturally the main industry in town with tobacco being the big deal.
Something Weird: One thing that CT snobs, like myself, like to point out is that South Windsor is actually NOT south of Windsor. It’s east. So it’s very improperly named. Also, South Windsor is home to the nation’s oldest operating post office. Hopefully when the post office closes for good, it’ll be the last to shut down.