In 1930, at the age of 23, Wainwright saved up enough money for a week's walking holiday in the Lake District with his cousin Eric Beardsall. They arrived in Windermere and climbed the nearby hill Orrest Head, where Wainwright saw his first view of the Lakeland fells. This moment marked the start of what he would later describe as his love affair with the Lake District. In 1931 he married his first wife, Ruth Holden, a local mill worker, with whom he had a son Peter. In 1941 Wainwright was able to move closer to the fells when he took a job (and with it a pay cut) at the Borough Treasurer's office in Kendal, Westmorland. He lived and worked in the town for the rest of his life, serving as Borough Treasurer from 1948 until he retired in 1967. His first marriage ended when Ruth walked out three weeks before he retired. They later divorced. In 1970 he married Betty McNally, also a divorcee, who became his walking companion and who eventually carried his ashes to Innominate Tarn at the top of Haystacks.
According to Wainwright in his autobiography Fellwanderer, he initially planned the series for his own interest rather than with any intention of publication. When he did come to publish his first book it was privately through a local printer, as he could not face the prospect of finding a publisher; however, 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 editions. This arrangement continued for the first editions of the next three books in the series, after which they were taken over by the local newspaper The Westmorland Gazette in Kendal. Wainwright's books were in turn taken over by Michael Joseph in the 1990s. When they ceased publication in 2003, the rights were bought by Frances Lincoln.
The Pictorial Guides are currently being updated, for the first time since their original publication, to take account of changed conditions on the fells. The revisions are being made by Chris Jesty, who uses an imitation of Wainwright's hand lettering to make the alterations look as unobtrusive as possible. Perhaps the most notable change is that the covers of the revised books show photographs of the Lake District by Derry Brabbs, rather than the drawings that were on the covers of the originals. As of July 2008 the first five books in the 'Lakeland Fells' series have been issued in a revised edition, with the sixth book due to be published on 23 October 2008 and the seventh in Spring 2009. Revised editions of the remaining guides, including The Outlying Fells of Lakeland are planned to be published by 2012.
In 1972 Wainwright devised the Coast to Coast Walk, partly as a conscious alternative to the Pennine Way. The Coast to Coast, he declares in his guidebook to the route, which follows the same format as the Pennine Way Companion, "puts the Pennine Way to shame" for scenic beauty, variety and interest. The 190-mile route traverses the north of England from St. Bees to Robin Hood's Bay, passing through the Lake District, the Yorkshire Dales and the North York Moors national parks.
The Outlying Fells of Lakeland (an idea he had previously rejected), published in 1974, was his last major guidebook. Thereafter he concentrated on sketchbooks of larger-size line drawings until his eyesight began to fail in the mid-1980s. His Ex-Fellwanderer, an autobiographical work published in 1987, was clearly intended to be his last written work – to the relief of some, shocked by the misogyny and right-wing views it revealed – but he continued to lend his name and some written commentary to a series of "coffee table books" featuring the photography of Derry Brabbs. Although commercially successful, these were not highly regarded by fans of Wainwright's earlier work as they contained little new information and the octogenarian's prose had become stilted and humourless.
A BBC documentary has been shot about Wainwright's life and was aired on Sunday 25 February 2007 on BBC Four, prior to a new 4-part series of walks beginning on Monday 26 February 2007.
This first Wainwright Walks BBC series covered Blencathra by Sharp Edge, Castle Crag, Haystacks and Scafell Pike from Seathwaite. The second series, broadcast later in 2007, includes Catbells, Crinkle Crags, Helm Crag, Helvellyn from Patterdale, High Street from Mardale and Pillar. A third series is currently in production (Aug 2008). The presenter is Julia Bradbury. A Granada TV series Wainwright Country included Eagle Crag, Great Calva, Knott Rigg, Pike O'Blisco, Stybarrow Dodd, Thornthwaite Crag and Yewbarrow.
Wainwright Walks Series One was released on DVD in June 2007 and Series Two will be available in early January 2008.
Wainwright died in 1991 of a heart attack. According to his biographer Hunter Davies he failed to leave anything to his son Peter, the product of his first, unhappy marriage.
Wainwright's Pictorial Guides have been in continuous publication since they were written and have sold more than two million copies. Although a large number of more up-to-date guides are now on the market, his books remain among the most popular available for their depth, detail and unique style. Moreover, his division of the Lake District into seven areas, and his choice of fells to include, have been followed in whole or in part by subsequent writers such as Mark Richards. The Coast to Coast Walk too is one of the most popular long-distance footpaths in the United Kingdom despite its lack of official status, and has spawned various guidebooks by other authors. In 2003 it was voted the second best walk in the world in a survey of experts conducted by Country Walking magazine. The popularity of Wainwright's books of drawings and large-format photographic books has not matched that of the guides, however, and many of these are now out of print.
The 214 fells described in the Pictorial Guides are now generally known as the Wainwrights, and visiting them all is a common form of peak bagging. The Long Distance Walkers Association maintains a register of walkers who have completed the Wainwrights; in November 2007 there were 459 people on the list, of whom 40 had completed more than once. Dave Hewitt estimates that the total number of completers could be over 50% higher than the LDWA's figure. 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.
Wainwright was a strong supporter of animal rights, and gave most of the profits from his books to animal charities. In 1972 he became chairman of the recently founded Animal Rescue Cumbria, and over the years he donated enough money to the charity to enable the foundation in 1984 of Kapellan, a shelter for stray cats and dogs in Kendal. After his death the society was renamed "Animal Rescue Cumbria – The Wainwright Shelter" in his memory.
The Wainwright Society was inaugurated in 2002, with the aim of keeping alive the things he promoted through his books.
This is a list of the principal books by Wainwright published in his lifetime. He also produced several further books of drawings and illustrated works by other authors notably "The Plague Dogs" by Richard Adams in which his maps are fairly essential for following the dogs' progress .