Londonist recently produced this Medieval Tube Map, which synthesizes medieval place names located in central London throughout the Middle Ages (they considered roughly 400-1600) with the modern Tube Map. I think this is a great example of giving context to the historical past, by providing something immediately recognizable to the contemporary Londoner. The overlay of something quite technological, like the London underground system, over medieval place names may seem disjointed at first, but ultimately it brings with it a greater level of access since any rider of the tube is deeply familiar with the map and many regular riders would be able to orient themselves spatially to the landmarks above ground (memory being best housed in something visual and spatial).
If we consider another Londonist offering, the Anglo Saxon London Map: Updated, below, it reads in a very different way to the Medieval Tube Map. Now, London is much less recognizable to today's inhabitants and tourists, which is rendered predominently green with forests and far-apart houses -- the only thing that I make out immediately is the U-shaped curve of the Thames at the Isle of Dogs in East London.
The innovative and more accessible approach of the Medieval Tube Map can be an interesting way to give context and comprehensibility to GIS work in the historical humanities, as well as to provide a more approachable framework to students who are unlikely to come across drawn-out maps, as in the Anglo-Saxon example, in everyday life.