The first settlement – Hailes (“mounds” or “hillocks”) – was sited in a wooded glen at the foot of the Pentlands next to a ford straddling the Water of Leith. A church was constructed at the end of the 11th century at the current site of St Cuthbert’s Parish Church by Ethelred, the third son of Malcolm III (chief constructor of Edinburgh Castle) and his wife Margaret. In the 12th century, Norman barons introduced the feudal system. By the 14th century, the village was named Colbanestoun (after a notable resident, Colban), later contracted to Colinton.
By the 15th century, water mills for waulking cloth and grinding grain had been built along the Water of Leith and adjacent marshes drained for pasture. The castle (now on Merchiston School’s grounds), built in the late 15th Century, became important and was frequented by James VI in the late 16th century.