It's not really 'to do with' the settlement, but it features silently as the landing spot in a strange tale. This is what allegedly happened:
The story runs that [Robert] Willance, who was a successful lead miner, was out hunting when the moors became enveloped in fog. However, he galloped on towards the cry of hounds in front to the edge of the precipitous cliff. Unable to pull up the horse went over, and falling the 200 odd feet to the valley below was killed outright. The rider escaped with a broken leg, and tradition says he lay where he was for three days, blowing his horn at intervals to call aid. It is hardly likely he would escape the search parties who would certainly scour the district for him, so long, but let that pass. Another local tradition is that he cut open the belly of his horse and put his fractured limb inside to preserve it from the frost. Anyhow it had to be amputated and was buried in Richmond churchyard till such time as its owner should complete the interment. This took place on Feb. 12, 1615, Willance having in the meantime become an alderman of his native town and having had three stones erected at the place where his horse took its fatal jump. Each stone was placed twenty-four feet apart, and two of them were inscribed: "1606: Glory be to our merciful God, who miraculously preserved me from the danger so great."
The whole thing sounds very fishy to me, including the stoney bit - why was the horse leaping for one thing? But I shouldn't question it as the locals love it - they erected another stone there in 2006.
The story above is courtesy of J Fairfax-Blakeborough, in Notes and Queries for Sept. 26th, 1925.
According to the monument description on Magic... finds have suggested this is a Romano-British enclosed agricultural settlement that began life in the Iron Age. Its back edge is against the scree slope of Whitcliffe Scar, and below it is the River Swale - it's got clear views up and down the valley.
'Substantial stone rubble ramparts' mark out two rectangular enclosures separated by a deep hollow way. There are some weird linked chambers in the eastern side, and you can see traces of a variety of buildings in both enclosures.