The Winnie-the-Pooh stories are set inAshdown Forest,East Sussex, England. The forest is an area of tranquil open heathland on the highest sandy ridges of theHigh Weald Area of Outstanding Natural Beautysituated 30 miles (50 km) south-east of London. In 1925 Milne, a Londoner, bought a country home a mile to the north of the forest atCotchford Farm, nearHartfield. According to Christopher Milne, while his father continued to live in London "...the four of us – he, his wife, his son and his son's nanny – would pile into a large blue, chauffeur-driven Fiat and travel down every Saturday morning and back again every Monday afternoon. And we would spend a whole glorious month there in the spring and two months in the summer."From the front lawn the family had a view across a meadow to a line ofaldersthat fringed theRiver Medway, beyond which the ground rose through more trees until finally "above them, in the faraway distance, crowning the view, was a bare hilltop. In the centre of this hilltop was a clump of pines." Most of his father's visits to the forest at that time were, he noted, family expeditions on foot "to make yet another attempt to count the pine trees on Gill's Lap or to search for the marsh gentian". Christopher added that, inspired by Ashdown Forest, his father had made it "the setting for two of his books, finishing the second little over three years after his arrival".
Many locations in the stories can be associated with real places in and around the forest. As Christopher Milne wrote in his autobiography: "Pooh’s forest and Ashdown Forest are identical". For example, the fictional "Hundred Acre Wood" was in reality Five Hundred Acre Wood; Galleon's Leap was inspired by the prominent hilltop of Gill's Lap, while a clump of trees just north of Gill's Lap became Christopher Robin'sThe Enchanted Place, because no-one had ever been able to count whether there were 63 or 64 trees in the circle.
The landscapes depicted inE. H. Shepard's illustrations for the Winnie-the-Pooh books were directly inspired by the distinctive landscape of Ashdown Forest, with its high, open heathlands of heather, gorse, bracken and silver birch, punctuated by hilltop clumps of pine trees. Many of Shepard's illustrations can be matched to actual views, allowing for a degree of artistic licence. Shepard's sketches of pine trees and other forest scenes are held at theVictoria and Albert Museumin London.
The game ofPoohstickswas originally played by Christopher Milne on the wooden footbridge,across the Millbrook,Posingford Wood, close to Cotchford Farm. It is now a tourist attraction, and it has become traditional to play the game there using sticks gathered in the nearby woodland.When the footbridge had to be replaced in 1999, the architect used as a main source drawings by Shepard in the books, which differ a little from the original structure.