While most of his classmates were obliged to find employment in the local mills, Wainwright started work as an office boy in Blackburn Borough Engineer's Department.
He spent several years studying at night school, gaining qualifications in accountancy which enabled him to further his career at Blackburn Borough Council.
In 1930, at the age of 23, Wainwright saved up for a week's walking holiday in the Lake District with his cousin Eric Beardsall.
In 1941 Wainwright moved closer to the fells when he took a job (and a pay cut) at the Borough Treasurer's office in Kendal, Westmorland.
In 1970 he married Betty McNally (1922–2008), a divorcée, who became his walking companion and who carried his ashes to Innominate Tarn at the top of Haystacks.
[citation needed] On Desert Island Discs, he described himself as having once been shy but having grown up to be antisocial and would avoid speaking to others, even lone walkers on fell tops.
[10] He planned the precise scope and content of the seven volumes and worked conscientiously and meticulously on the series for the next 13 years at an average rate of one page per evening.
His friend Henry Marshall, Chief Librarian of Kendal and Westmorland, took charge of publicity and administration, and his name appears as publisher on the early impressions.
The revisions were made by Chris Jesty, and the publishers used an imitation font of Wainwright's hand lettering to make the alterations look as unobtrusive as possible.
Wainwright followed the Pictorial Guides in 1968 with the Pennine Way Companion, applying the same detailed approach to Britain's first long-distance footpath.
Bees to Robin Hood's Bay, passing through the Lake District, the Yorkshire Dales and the North York Moors national parks.
By the mid-1980s Wainwright was a TV personality; he featured in three television series for the BBC, presented by farmer and broadcaster Eric Robson and devised, directed and produced by Richard Else.
[12] Although a number of more up-to-date guides are on the market, his books remain among the most popular for their depth, detail and unique style.
His division of the Lake District into seven areas, and choice of fells to include, have been followed in whole or in part by subsequent writers such as Mark Richards.
[25] The Ramblers Association reported in 2008 that a boy of six years, four months and 27 days had become the youngest person to complete the Wainwrights.
[8] In 1972 he became chairman of Animal Rescue Cumbria, and donated enough money to enable the foundation in 1984 of Kapellan, a shelter for stray cats and dogs in Kendal.