Both of the above maps, of Summit, NJ, are from the New York Public Library Digital Collection. The NYPL has a lot of interesting projects going on encouraging the public to play with the huge array of resources stored in their archives.
There are many other ways to make cool maps, such as this one by Nobutaka Aozaki, a map of Manhattan composed of hand-drawn maps by various New York pedestrians whom the artist asked for directions.
The artist has a short video, and photographs documenting his process here. The piece is called From Here to There.
I got the following from the interesting book Drawings on Geology.
Cornell University Library’s Digital Collection has a collection called “Persuasive Maps: PJ Mode Collection.” Two are below.
Here’s a nice hand-drawn map of Vienna:
Here’s a more allegorical, imaginary one:
More map collections and articles
“Why do so many people love making maps?” (from Bookforum‘s “Omnivore” blog)
Flowing Data has a nice collection of resources on maps.
There are many educational and scientific collections on maps, but here are a couple:
Here’s a map I made of Summit, NJ with Stamen:
Here are more map links
Wanderlust, famous journeys mapped in an interactive feature by Good
more illustrated maps, including tutorials.
Map reading guides from the Ordinance Survey (British)
also read: “California as an Island” in The Partly Cloudy Patriot by Sarah Vowell