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Well, being as it was a war forces from one side or another would attack a certain location – usually something strategically important, such as a castle – and sometimes capture it.
That’s what happened to Bridgnorth shortly after the date on the map. It was held by Royalists, and the Roundheads came along and decided they didn’t want a Royalist stronghold at this vital crossing of the River Severn.
Now, Bridgnorth castle was built on top of a cliff, the foot of which is mere tens of metres from the river – a really good vantage point for the crossing and for ships sailing up the river (it’s called Bridgnorth because it’s where the bridg~~e~~ is that is as far north as could be sailed up the Severn at the time).
So the Parlimentarians came along and surrounded the town, with the Royalists all penned up inside the castle. It looked like it could be a seige, and that’s no good, it takes forever and ties up troops and requires good supply lines. So the Roundheads had two prongs of attack. One was to build a big old flat-topped hill, now called “Panpudding Hill” (and fantastic for tabogganning down when it snows since it has a uniform slope most of the way down). On top of Panpudding Hill they put a couple of trebuchets and fired stuff over the castle walls from there. This didn’t work, though it was partially reenacted in 2002-ish by TimeTeam, facing the other direction and therefore firing into an empty field, and using flaming melons.
I digress. The second approach was to go into the caves in the cliff (used at various points in their history for living space and for a church, in the case of the largest, though I don’t recall whether that was before or after the civil war, or both). They climbed up to the top of the biggest cave, not that far under the castle, and started digging a tunnel. They dug day and night, and the castle’s inhabitants could hear them. The castle defenders surrendered before the planned planting of gunpowder down there, and so the tunnel remains intact (though inaccessible these days).
Rather than garrison the castle and expend troops in the process, the Roundheads used that gunpowder they had planned on putting in the tunnels inside the castle itself instead. They blew it sky-high, and now [this](http://imgur.com/iCJZ1vm) is all that remains.