Wensleydale was the home of one of Yorkshire's most famous clans, the Metcalfes, after they emigrated from Dentdale. The Metcalfe Society hold records dating back to Metcalfes living in the area during the 14th century. They were one of the most prominent families in Yorkshire for more than five centuries. Sir James Metcalfe, who was born and lived in Wensleydale, was a captain in the army which fought with King Henry V in the battle of Agincourt in 1415. A fortified manor, Nappa Hall near Askrigg was built by his son Sir Thomas Metcalfe. Metcalfe is still one of the most common surnames in Yorkshire. Bolton Castle, in the village of Castle Bolton, is a notable local historic site. Building of the structure was begun by Richard le Scrope, Lord Treasurer and Lord Chancellor to Richard II, in 1378. The building was finally completed in c.1399; the total cost was approximately 18,000 marks. Mary, Queen of Scots, was imprisoned there for six months, ending in January 1569, under head keeper Sir Francis Knollys, housed in the apartment of Henry Scrope; she was allowed a retinue of 51, with 30 housed in the castle. The story goes that she once escaped and made her way towards Leyburn but was captured at a spot on "The Shawl" called "Queen's Gap".
Wensleydale is a very popular destination in its own right, enhanced by its central location between two other well-known tourist dales: Wharfedale and the quieter Swaledale. Wensleydale is a common destination for visitors who like walking on mountains, moorland, dale-sides, and valley bottoms. Hawes and Leyburn are popular because of their age, location and facilities. Hawes is the home of rope maker, where visitors can see the manufacturing process. Hawes is also home to the Wensleydale Creamery, the Dales Countryside Museum, shops and many of places to eat. Part of Bolton Castle is a ruin but the other section has been restored; this attraction had a 4.5 star rating in mid 2018 by the users of TripAdvisor who had visited the castle. The Wensleydale Railway operates in Wensleydale. It currently runs between Leeming Bar, the A1 and Redmire, near Castle Bolton. The railway's long-term plan is eventually to run the whole length of the valley and connect again with the National Rail network at both ends: at Garsdale on the Settle-Carlisle Railway in the west and Northallerton on the East Coast Main Line in the east. It is hoped this may help relieve some of the current traffic congestion that the valley suffers from during the busiest months. Some visitors come to Wensleydale due to its connection with Richard III, who was brought up in Middleham Castle. It has the largest castle keep in the North of England. Middleham itself is a market town with pubs and horse-racing connections. In the market place stands a stone carving, believed to be a boar's head, signifying where the animal market was during the 15th century as well as representing Richard's personal standard, the white boar. Each August, visitors and local people gather at the edge of Leyburn for the Wensleydale Agricultural Show. The 2018 event was scheduled for 25 August.