The earliest known reference to the Farmer’s Boy is in 1862, although it is believed to be older than that. Papers for the Crown Brewery, owned by Thomas Driver Medcalf of Ware Road and Railway Street in Hertford, show that the Farmer’s Boy was known as the Woodman until sometime before 1871. Kelly’s Directory of 1870 lists by name the Farmer’s Boy as a public house, run by Thomas James Harrison; up until then it was listed in Kelly’s simply as an unnamed beer house. In 1885 Thomas Harrison and George Bird appear to have been the tenants. The present building includes what was originally the pub as well as a small cottage, a stable and a shed.

The Crown Brewery, including the Farmer’s Boy, was sold to Percy Hargreaves of Abridge, Essex, in about 1885, and in 1895 Benskins purchased the brewery and closed it. Hertford Museum has a copy of sale particulars, dated 16 December 1895, for the Crown Brewery and nine public or beer houses including the Farmer’s Boy, which contained bar and parlour, tap room and cellar; kitchen and 5 bedrooms, stabling, gardens and outbuildings; also a cottage let to a Mrs Bird. At some stage the Farmer’s Boy was acquired by the Waltham Abbey Brewery since McMullen’s purchased the Waltham Abbey Brewery, including the Farmer’s Boy, in July 1898. In 1918 the keeper was a Miss Elizabeth I Webb, and in 1937 it is Robert John Brighty. McMullen’s sold the Farmer’s Boy in October 1990, when it closed for refurbishment and reopened as a free house in 1992. As of February 2017 father and son, Kevin & Mitch Brummitt own and operate the site.