When Tomintoul was founded in the late eighteenth century by Alexander, 4th Duke of Gordon, the Main Street was laid out along the line of the public road, which at that date comprised a stretch of the military road built in the 1750s to link Coupar Angus and Fort George.

The street is unusually wide, measuring approximately 13m across. The house plots laid out along its length were also unusually broad, each plot measuring 22m in width, giving rise to the 'house-cum-half-house' plan characteristic of Tomintoul. The original terms of the feu stipulated that the houses were to be built facing the street, but some evidently disregarded this instruction and built them with their gables end-on to the street.

Some of the cottages on Main Street are of early nineteenth-century date, forming part of an early phase in the village's history.