Here's an early iteration of the joke about there being a Nantucket subway, from Northeastern's 1968 yearbook.  Today, there are whimsical maps of the Nantucket subway, and if you'd like to redecorate with Nantucket Subway ceramic tiles, they actually exist!

"In the map your heart is taking the curves.  Sometimes you miss one in the borderlands.  Sometimes you get there with the help of the saints."  From Mothers News, 2013.

From Nebelspalter, 1886.

Yes, Google Maps blurred the face of this giant mascot, because giant mascots are entitled to privacy, too.

If we're to trust Google Maps, this place is either "Desert Oraoracle" or "Desersert Oracle," depending upon how you approach.  Note that there are two mail slots on the door, presumably one for each parallel universe.  Here's the link, not that you wouldn't believe us.  [Update: they saw my post and fixed the glitch!]

From Duke's 1914 yearbook.

X marks the spot.  "We all know it's more than just a location on the map of Arizona."  From the Phoenix yearbook of 1951.  For over 80 surprising meanings of the letter X, see One-Letter Words: A Dictionary.

Before "What Happens in Vegas, Stays in Vegas" (2003), there was Mexico's mysterious triangle of silence.  From UFO Newsclipping Service, 1982.

The endpapers from Barnard's 1929 yearbook.

Here's a blank map from Jim White's No Such Place album.

In our photo of chronologician Michael, he is not actually looking at his invisible watch but rather consulting the living map that he's wearing.  (A living map never gets outdated but rather, remaining mysterious to its core, is a provocation to experience, casting as it does the luminosity of presence.  A living map is full of latencies, providing criteria by which a competent discoverer may test his projected conjectures.)

From East Carolina's 1934 yearbook.

Here's a map of the fictional town of Tutter, Illinois (inspired by the author's childhood in Utica).  From the endpapers of Jerry Todd, Editor-In-Grief by Leo Edwards, 1930.