Further to "Exploring Boston: Mapping the lost 'Boston Neck'", I discovered a new map blog, specializing in zoomable images of (mostly) old and ancient maps.
Despite a very dorky name, "The Big Map Blog" is pretty good, and recently featured two British maps of revolutionary Boston:
I also recently finished a book on mapping: A History of the World in Twelve Maps, By Jerry Brotton. (ISBN13: 9780670023394).
In it, the author selects 12 major maps (and many minor ones) to show how humanity's view of its home planet evolved from Ptolemy's maps through Google Earth. Along the way, the book answers many questions such as why North is now usually shown on top (it wasn't always so), and how evolving technologies (e.g. hand-drawn ink on paper, woodblock, copperplate, digital... ) affected map making.
Brotton does a pretty good job of showing how a culture's literal word view often affected its maps; maps could be (and were) often more symbolic and notional than anything you could use to find your way from one place to another. For example, medieval maps often were more intent on showing you your place in the next world (the afterlife) than showing you were you actually were in this one.
The book was worth reading, but I found it very uneven, feeling less like a holistic book than a series of separate articles written at different times. (Maybe it was.) There were variances in tone, too. For example, the author is academically neutral about, say, the Dutch maintaining extreme proprietary control of their maritime maps during the height of their power (Dutchmen could be executed for letting a map fall into the hands of economic rivals); but he's is clearly very unhappy with and biased against Google's retaining proprietary control over the internal workings of its Google Maps and Earth.
(Perhaps it has something to do with the fact that in Google Maps and Earth computer scientists have somewhat displaced academic cartographers....)
So, it's not a great book, but it is an interesting one, and worth a read, if maps interest you.