As discovered on the website Link
The legendary Cupid's Hill and equally legendary landlord and undertaker Joe take equal precedence for this once in a lifetime pub. For that I mean you only had to visit this place once for it to be etched into your mind. The pub was a timewarp with settles and table skittles and some really old bottles of an obscure Whitbread beer on the counter. But no one went there for the beer. Cupid's Hill Inn was a cider house with bottles of Westons and one year a wooden cask of perry on the bar, made with pears from the back garden and pressed by Denis Gwatkin. Another year some American tourists turned up at the Inn and asked to see the 'cockpit', Joe took them outside and showed them a hole in the ground, at which the Americans asked where the rest of the aircraft was! Obviously tourists are not familiar with some of the more traditional pub games played on the Monmouthshire/Herefordshire border. When the ancient locals, all sitting around the fireplace on a cold Saturday lunchtime, recanted this story to me, I pointed out that cockfighting had been illegal since the 1820s, “Nay we used to have it 'round 'ere up to the 1950s, in fact we tried the other night to get the cockerels to fight in the pub but they weren't having none of it!” The thought of the police and RSPCA raiding this pub in the early hours of the morning to find the cider-sodden regulars arranging an animal fight sprung to mind. What did close the Inn was the death of the landlord Joe and the former Inn is now a private house.
The pub sign bracket can still be seen as can a glimpse of the view over the Monnow valley towards Garway Hill.