Here are fifteen strange town names:
http://www.oddee.com/item_96555.aspx
When my wife was pregnant with our first, we were driving across Canada to PEI. Along the way, we'd look at maps and signs to help come up with names for our soon to arrive son. Not sure why, but my wife rejected Heart's Delight (NFLD) and was really worried about people getting the wrong idea when I suggested Come By Chance (NFLD).
Don't worry, we gave him a normal name (Nathaniel)