Once Milne had created the literary landscape of the hundred acre wood and surrounding features, it was Shepard who firmly established the visual setting. With typical Shepard humour the map is supposed to be the work of Christopher Robin ("Drawn by me and Mr Shepard helpd") and includes a number of Christopher Robin’s own spellings ("piknicks", "raletions" and "rox").

The map was reproduced on the endpapers of Winnie-the-Pooh and, at least for Shepard, established a definite visual style. In 1931 when Shepard worked on The Wind in the Willows his first innovation was to introduce a map of the locality on the endpapers. Both maps, of course, pre-date those in Tolkien’s The Hobbit.

Just as Shepard’s map is the means of entry to the book, it is also the first animated sequence in the Disney film (Winnie the Pooh and the Honey Tree, 1966).

Shepard produced at least two preliminary drawings for the map (one in the collection of the V&A Museum and an earlier sketch sold in these rooms, 17 December 2008). This, the original as used by the publishers, was sold by Shepard in his exhibition at The Sporting Gallery, 26 November – 21 December 1926. It was given the title, in the exhibition catalogue, as simply "Map of Pooh’s Country". Below the mount Shepard has added the caption "Winnie-the-Pooh. Map for end papers". The reverse of the board also notes "Map for End Papers".