Part x in the occasional series on maps; this one is a 2D route cutting through a 3D landscape from Ogilby’s Britannia dating from 1675, and a predecessor of the modern motoring atlas. This particular map dates from a time when the hill was traversed only by those who were prepared to run the risk of a 17th century style stop-and-search at the hands of the highwaymen most likely laying in wait behind an oak tree somewhere in the woods by the side of the road (presumably the hill was completely wooded at that time?).
Judging by Ogilvy’s map, he didn’t appear to be overly concerned by the risk of highway robbery on the London-Dover route, because he might have added an alternative route alongside the river if he was.
I’m hoping to see the original map at some point as in this reproduction it’s not possible to make out the writing above the mountainous section that portrays Shooters Hill, it looks like it says “To ***** West”, but East Wickham and Wellen (about 6 houses comprising what we now call Welling) are clearly legible here.
The site this map was copied from also included a section from a 1652 book detailing the adventures of a highwayman called James Hind, including one escapade where he conducts a hold-up on the hill as part of his robbers apprenticeship:
Now they go to Shooters-Hill[1. The most notorious spot in England for robberies on the highway], where presently they discovered a Gentleman and his servant coming towards them; and Allen bid Hind to ride alone up to them, and they would lie in an Ambush if occasion should serve; thereupon Hind rides to them (being already tutor’d to the purpose) and bids them Stand, and deliver such money as they had, otherwise he would presently be their death; The Gentleman not willing to die, presently gave him Ten pounds, which was all the Gentleman had; Hind seeing it was all he had, said, Sir, here is forty shillings for you to bear your Charges; in regard it is my Handsale[2. Handsale: handsel, hansel: gift given for luck.]; the Gentleman answered, I wish you better luck with it then I have; so Hind took his way, and came to the rest of the gang; and Allen praised him for learning his Art so quickly, saying, did you not see, How he rob’d him with a Grace.