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Whilst out on Winter Hill last night the MNPR stopped at "Two Lads". Which got is discussing why it got it's name.
The legend of Two Lads:
There are a couple of local “legends” featuring the Two Lads, perhaps the best known being the least well known - because there’s several conflicting versions. The basic story goes that “two lads” where stuck on the moor and froze to death on the site currently marked by the large cairn. The difference in versions are when this was supposed to have happened.
The earliest tale relates that two princes of a Saxon king dies on the moor, which would, based on other local legendary dates be around 680 CE. The next tale states the lost lads where the sons of Bishop Pilkington so maybe around 1540 CE. The story that was often told in Bolton was that the two lads where children working in a mill over the Belmont side of the hill that were forced to walk back from work each day over the moors.
What have you got?
I rather liked the story of Joe's Cup that @duncancallum told us last time we were in the Rivvy area. I don't remember the detail, perhaps he'll chip in but this is it. 
Winter Hill / Rivington does seem rich in this sort of thing.
https://en.wikipedia.org/wiki/Winter_Hill_air_disaster
https://www.anglezarke.net/places/bomber-zulu/
Joe's Cups a local fell runner who stashed a tin mug up and used to drink from the stream.
That side of the hills full of stuff.
The ruins up onto spitlers is cald old Rachel's.
Winter hills been farmed and mined for thousands of years.
Couple of good UFO stories too
The Devil's Punchpowl in Hindhead/Surrey
According to one story, the Devil became so irritated by all the churches being built in Sussex during the Middle Ages that he decided to dig a channel from the English Channel through the South Downs and flood the area. As he began digging, he threw up huge lumps of earth, each of which became a local landmark — such as Chanctonbury Ring, Cissbury Ring and Mount Caburn. He got as far as the village of Poynings (an area known as the Devil's Dyke) when he was disturbed by a cock crowing. (One version of this story claims that it was the prayers of St Dunstan that made all the local cocks crow earlier than usual.) The devil assumed that dawn was about to break and leapt into Surrey, creating the Devil's Punch Bowl where he landed.
Another story goes that, in his spare time, he hurled lumps of earth at the god Thor to annoy him. The hollow out of which he scooped the earth became the Punch Bowl. The local village of Thursley means Thor's place.<sup id="cite_ref-11" class="reference">[11]</sup> An alternative version of this story says that Thor threw the earth at the Devil, who was annoying Thor by jumping across the Devil's Jumps.
Also not really a legend, but above the Punchbowl itself is Gibbet Hill and the Sailor's stone https://en.wikipedia.org/wiki/Unknown_Sailor
Lovely spot on a sunny day, but on a solo night ride, when the wind is in the trees, I always seemed to manage to up the wattage a bit to get past quickly......
Margate had one once.
https://www.esquire.com/uk/culture/news/a18650/marget-im-a-legend-man-tasered-video/
I often ride or run through a place called pennycomequick.
I cannot confirm is this is fact or fiction.