During the first half of the eighteenth century the political and social climate of Scotland was becoming increasingly favourable for the expansion of agricultural output and mineral exploitation. These activities generated extra traffic and the growing number of wheeled vehicles created a demand for soundly constructed roads. In contrast with the English parish system, responsibility for road management in Scotland lay with landowners, accountable to their county meetings. A tax on rent financed a selective programme of improvement, and when parish labour was converted to a monetary payment a considerable increase in road works became possible. In Fife, the influence of farmers and coal owners is seen in the planning of roads to distribute lime and coal, while leading landowners were concerned with the national highways which crossed the peninsula. Although one of these became a toll road in 1753, the turnpike system was adopted for the county only at the end of the century. It is the hitherto underestimated activity among road authorities before the imposition of tolls which forms the main theme of this study. The basic pattern of overland connections existing around 1700 is derived from the evidence of settlement distribution and known physiographic constraints. This pattern is checked against the earliest available maps and road records to deduce a putative network. A sequence of maps illustrates the subsequent changes, including the extent of postal and coach services and control of roads by the turnpike trusts. The abandonment of hillside routes, the dominance of the link between the Forth and Tay ferries, and the influence of individual landowners on schemes of improvement are illustrated by more localised studies which emphasise the multiplicity of factors operating during a crucial phase in the development of the modern road network.