The borders of New Haven, Connecticut, like those of many other American cities, appear to be wildly irrational. Starting on the west side of New Haven harbor, the boundary follows the West River northward for slightly more than a mile, suddenly jogging west for two miles then continuing north and veering northeast. Before turning eastward, the line juts out to capture two oddly shaped protrusions in the northwest comer of the city. After traveling east for four miles the boundary banks 120° south to include a four mile-long, half-mile wide strip along the east side of the harbor. Somehow, New Haven has taken the shape of a pregnant kangaroo.
Glasgow, Joshua, "The Evolution of the Kangaroo: The History of Municipal Border Change in New Haven, Connecticut" (2004). Student Legal History Papers. Paper 36.