The Madison Chain of Lakes includes Lake Mendota, Lake Monona, Lake Wingra, Lake Waubesa and Lake Kegonsa. If you're talking to a boater or fisherman, they will just use the term "Madison Chain". These lakes are all very popular recreational lakes.
A nickname for the city of Indianapolis, a reference to the circular shape of its city limits.
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.
(noun) Common term for hamburger in much of Maine, especially when used as an ingredient or topping (as in hamburg pizza).
A coffee crawl is like a bar crawl, but for coffeehouses. A local tour company, Seattle By Foot, stages these crawls on weekends, offering the opportunity to experience Seattle's coffee shops, which constitute ground zero for many coffee enthusiasts. And, yes, there's more than just Starbucks on the tour!