John was the owner of the Wellington Brewery in Denmark Street. Frederick Headington, John’s father, and his cousin, Richard Webster, had purchased the brewery in 1877 from Thomas Dunning. In 1889 the Headington and Webster partnership was dissolved and Frederick took over the brewery which he left to his son.
Under John’s management the business expanded considerably and, by 1911, it had entered the mineral water business. By 1920 John owned fifteen freehold licensed premises four of which were in Wokingham. His greatest coup was considered to be the purchase of the Pheasant in Winnersh from the Garth estate in 1912.
This widespread business employed a number of sales representatives who visited the public houses. During the First World War, when his representatives joined the armed forces, John took over this work using a Levis motor cycle, which he had purchased for £25, as transportation.
The Headingtons lived at Penventon in Finchampstead Road. Clara (b. 1871), John’s wife, was the third daughter of the Rev. Hugh McSorley of Tyrone and Vicar of St. Paul’s, Tottenham. They had two children, Myrtle Somerled (1900-1981) and Nigel Somerled (1903-1989). When Nigel was born John’s colleagues presented him with the unusual gift of a silver sugar basket and spoon. The basket is in the form of a Victorian rocking cradle. The cradle has since been given to the town and now forms part of the town’s regalia.
In addition to his civic duties John was agent for the Sun Fire and Life Assurance and manager of Wokingham Savings Bank. A keen sportsman and a fine horseman, he regularly rode with the Garth Hunt and the Berks. & Bucks. Farmers’ Staghounds until the Second World War.
John died on Thursday 9th March 1944, at the age of 78, in a nursing home and was buried in the family vault at Brookwood Cemetery. Penventon, which comprised three to four acres, was sold in the nineteen fifties. It is now Eastheath Gardens. The Wellington brewery building was later demolished, together with the Drill Hall, in 1979 to make way for a Tesco Superstore.