Even a brief look into the history and folklore of Roseberry Topping reveals a fascinating picture of this impressive local landmark. One interesting source of information is the 'Chaloner letter' written in early 1660's, which mentions Roseberry Topping, and noted that ...
"it hath somtymes had an hermitage on it, and a small smith's forge cut out of the rocke, together with a clefte or cut in the rocke called St. Winifrid's Needle, whither blind devotion led many a silly soul, not without hazard of a breaknecke tumblinge caste, while they attempted to put themselves to a needless pain creeping through that needle's eye."(Nichols, 1853)
The presence of a hermitage, and the 'blind devotion' of 'many silly souls' crawling beneath a rock dedicated to Saint Winifrid, points to this hill top having once being a religious site visited by pilgrims before the Reformation. There are no signs of the hermitage or other features on the hill top today, except perhaps for a rectangular section cut out of the rock near the modern trig point. This appears to be a much worn floor surface, and may be all that survives of the hermitage (or forge?). What became of Saint Winifrid's Needle is also unknown, it may have been destroyed after the Reformation, or by later quarrying. Another possibility is that the cleft was part of the cliff edge which collapsed after a massive lands slip in 1912. The Chaloner letter notes that there was a danger of people falling to their deaths as they crawled through the 'Needle's Eye', which suggests that it was on the edge of the crag high up on the hill.