The Plough was an old homestead at Winchmore Hill belonging to the Rogers family. Their front door once opened directly onto Wycombe Heath, but when the Heath was enclosed as part of the Amersham Enclosure Act of 1815, they were allotted 1 rood 36 perches of land (just under half an acre) immediately in front of the house. The Plough was given a beerhouse licence in 1830, but the beerseller, Caroline Rogers, supplemented her income by selling groceries.

Caroline Rogers died about 1870. It was probably at this time that Weller's Brewery bought the Plough. Their new tenant at The Plough was George Pursey, who supplemented his income by manufacturing chairs. He had a timber yard immediately to the east of the house and a saw-pit where trees were cut into planks to make chair seats. He also had a turning shop where the chair legs were turned on a lathe. George Pursey died in 1911 and was succeeded by his son Thomas Pursey. Thomas died in 1919, but the tenancy was taken over by his widow, Emma Pursey. The Plough was lot 69 in the sale of Wellers Brewery in 1929.

When Emma Pursey died in 1936, the Plough was continued by her son Frank, a carpenter and builder, until his death in 1961. More recently, the Plough was owned by the actress Barbara Windsor. After closing down briefly in 2008, it reopened as The Furrow but this too is now closed.