Nickname for Portland because of all the rainfall it receives. Puddletown has made its way into popular PDX culture, as it's commonly affixed to names of businesses, sports teams, et al.
A quintessential Rhode Island treat, made with milk and coffee syrup. Believe it or not, coffee milk is in fact the official state beverage.
Milwaukee nickname for a heavy citrus soda, such as squirt or 50/50.
Local nickname for the northernmost high school in the Peoria Public School District, Richwoods High School. Known for their association with the Peoria Country Club, even using their golf carts during their homecoming ceremony.
She-had-a-boy-again is a play on the Sheboygan's name. I heard of this recently when speaking with a friend of mine who's a Sheboygan native. As far as my friend knows, the meaning doesn't go any deeper than the phonetic relationship.