His father was a stonemason, often unemployed.  His mother was hardworking and god-fearing and raised him, along with his brother and two sisters, decently, but in somewhat poverty-stricken conditions.  They lived in a small cottage with no garden and no indoor bathroom.

His greatest joy was to copy drawings and cartoons from comics.  He became fascinated with maps and would walk up to 20 miles at a time.

He did very well at school, coming top of the class in most subjects, but left to earn his keep as an office boy in Blackburn Borough Engineer's Department.

He arrived in Windermere for a walking holiday with his cousin Eric Beardsall and they climbed the nearby Orrest Head - a hill 780 feet high.  Wainwright was enthralled by the view and this was a pivotal moment in his life that started his love affair with the Lake District.
They later divorced just before he retired and he married his second wife, Betty McNally, in 1970, who became his walking companion.

This enabled him to escape Blackburn and move to Kendal in 1941 when he took a job as an Accountancy Assistant at Kendal Borough Treasurer's Office.  He went on to become Borough Treasurer in 1948, remaining in this position until he retired in 1967.

Over the next 13 years he spent his weekends walking, collecting information in notebooks and in annotations on maps.  His evenings were spent drawing detailed maps, diagrams and landscape views.  These diagrams were compiled into the finished pages, along with his hand-written text, and published as A Pictorial Guide to the Lakeland Fells.  For this labour of love he was awarded the MBE.

He was also Chairman of Animal Rescue Cumbria, and gave most of the profits of his books to animal charities.
He created and wrote about 'A Coast to Coast Walk' which is one of the most popular long distance walks in the County - 190 miles long from St Bees, Cumbria to Robin Hood's Bay in Yorkshire.
There is a memorial to him in the church at Buttermere.  His ashes were scattered over Haystacks, his favourite mountain.