Wensleydale cheese was first made by French Cistercian monks from the Roquefort region, who had settled in Wensleydale. They built a monastery at Fors, but some years later the monks moved to Jervaulx in Lower Wensleydale. They brought with them a recipe for making cheese from sheep's milk. During the 14th century cows' milk began to be used instead, and the character of the cheese began to change. A little ewes' milk was still mixed in since it gave a more open texture, and allowed the development of the blue mould. At that time, Wensleydale was almost always blue with the white variety almost unknown. Nowadays, the opposite is true, with blue Wensleydale rarely seen. When the monastery was dissolved in 1540, the local farmers continued making the cheese until the Second World War, during which most milk in the country was used for the making of "Government Cheddar". Even after rationing ceased in 1954, cheese making did not return to pre-war levels.

In the 1990s, sales of Wensleydale cheese from the Wensleydale Creamery had fallen so low that production in Wensleydale itself was at risk of being suspended. The cheese experienced a boost in its popularity after being featured in the Wallace and Gromit clay-animated shorts A Grand Day Out, The Wrong Trousers, and A Close Shave, because of which the company survived. The main character of the series, Wallace, a cheese connoisseur, and inventor, mentions Wensleydale as a particularly favourite cheese. Animator and creator Nick Park chose it solely because it had a good name that would be interesting to animate the lip sync to rather than due to its origins in northern England where the shorts were set. He was also unaware of the financial difficulties that the company was experiencing. The company contacted Aardman Animations about a licence for a special brand of Wensleydale cheese called, "Wallace and Gromit Wensleydale", which sold well. When the 2005 full-length Wallace and Gromit film, The Curse of the Were-Rabbit, was released, sales of Wensleydale cheeses increased by 23%.

Very rational system where the fate of a 500 year old tradition relies solely on an animator finding the name funny.