Oldstead is a small settlement below the Hambleton Hills escapement but it has many unusual historic sites and buildings. In Medieval times, when it was named Stocking, it hosted the monks who would eventually move to Byland Abbey. Extensive water works and ponds still exist between Oldstead and Wass indicating the influence of the Abbey.
Oldstead featured in the Battle of Byland in 1322 when the Scots Army under Robert de Brus routed the English. Scotch Corner is a place name in the North West of the parish. This may commemorate the battle when the Scots climbed up a steep slope to cut off the English Army at the top but it may also be because a farm located here served refreshments to drovers over the years, many of whom would be Scots. A chapel was erected in 1957, using stone from the farm, by John Bunting, a sculptor, who decorated it with several of his sculptures and stained glass windows in memory of his school friends lost in WWII.
The Mount Snever Observatory was erected to commemorate the accession of Queen Victoria to the throne in 1837. It used to be a very visible landmark for miles around as it stands high above Oldstead. However it is now surrounded by many trees and has to be viewed close up.
A Methodist Chapel was built in Oldstead in 1868 due to disaffection with the church in Kilburn, the schooling of the children and the general rise in Nonconformity. It closed in 1960.
Oldstead Hall is a grade II listed Georgian Manor House with a Victorian wing and 4 medieval corbels within it. The Gallery in the hall grounds was a stable block but had its origins in a much older building. This general area is where the original monastery was situated.
Oldstead is now famous for the Black Swan which is a Michelin starred restaurant with rooms run by Tommy Banks using produce from the family farm. People come from all over Britain and overseas to sample his food.