Sheppard always carried a sketchbook.  The subject matter reflected wherever he happened to be: first and foremost around his locality in North West London – Bushey, Stanmore, Barnet, - and, especially after the purchase of his first car, (a Hill-man Minx) in 1954, sometimes further afield: Hertfordshire, Dunstable Downs and the Whipsnade area.“We often went out into the countryside, usually towards Hertford-shire as we lived in North West London.  My father always carried a sketch book, and some days in the summer he would sit and paint whilst we children played or went for a walk with our mother.” As a founder member of the Wapping Group, just before the war,  and in the decade which followed it, he painted numerous scenes along the river Thames in the East End of London.