I was walking North through the back streets of the City just a few days ago - from London Bridge to London Wall. It's amazing that so much of my route - zigzagging left and right through various junctions and down alleys - is clearly visible on an 800 year old map. I suspect none of the buildings are the same, but the roads are still there.
That reminds me of the trapezoidal Chrysler Building[1] in NYC, shaped by a plot boundary reflecting the pre-grid Boston Post Road[2] (only 2 weeks NYC-Boston!). The Road elsewheres reflects 1600's colonial improvements to the earlier Pequot Path, and influenced US1 et al.
I remember reading about an archeological dig in an intersection in the old part of Damascus. They dug down though a few thousand years of accumulated soil and found nothing.
That was by far my favorite part of visiting London, you could really feel and see how much of the city was still as it has been for a thousand years...just the penny rooms are now luxury flats.