A locals' local
Much of the history of the Jolly Farmer has, like those who frequented it, passed away with time. What we do know is that Cookham Dean was on the wool pack way - the mediaeval horse route used to transport wool from the West Country that climbs up through Quarry Woods and then through the village - and that at Sterlings in the village centre, the monks built a hospice to give the travellers a night's rest before the final leg of their journey to London.
We also know that in the 1800's the Dean was a fairly wild place full of hoards of itinerant workers who arrived each year to help strip the village cherry trees of their fruit. The wool packers, the cherry pickers and the villagers themselves would have needed somewhere to drink & socialise and Roger Parkes in the book 'Alice Ray Morton's Cookham' notes that an ale house, run from one or both of the cottages that form the current building and known as 'The Jolly Beer House' was sited close to the hospice to supply its guests with their needs.
Its position in the heart of the village suggests that it was always at the centre of local activities. Not that they were necessarily approved of; one of the reasons why the vicar at the time, The Rev. George Hodson, championed the need for a larger church in the village centre during the 1840s was that he was so appalled by the unruliness of its locals. What part The Jolly Beer House played in this is conjectural, but Friday & Saturday nights in its tiny bar must have been an unforgettable experience ... much like today.
It was renamed 'The Jolly Farmer' in the 1870's by its landlord, "Comfort" Parsons, its location close to the baker and the church - made it the natural place for a village pub. The butcher would come up from Cookham Rise with his meats delivery on his horse & cart. The baker was Mr Deadman and he would deliver either with his van or horse & cart. The milk came from Mr & Mrs Hollyer at the landlord and landlady at The Jolly Farmer. The milk came from churns; you'd hand over your jug and they'd fill it with a ladle.
They had a little shop at the side of the pub which was for dairy produce. The Hollyers were also local farmers which is where the name Jolly Farmer may have came from. Although we'll never know for certain, it's pretty clear that its always been a locals' local and a key part of the village and a focal point for its community.