This article explores the perspicacity of the ‘path‐dependency’ thesis for explaining pre‐ and post‐retirement migration, extending existing debates in the literature on path‐dependency retirement regions. The article presents a case‐study of pre‐ and post‐retirement migration to the Isle of Bute, Scotland. Drawing on findings from a household survey and biographical interviews with in‐migrants to the island, we ground our understanding of path‐dependency processes in individual behaviours and experiences, to demonstrate how specific attributes of particular places lay the foundations of path‐dependent migration flows. Our findings support the path‐dependency thesis, as applied to migration into rural areas, demonstrating how the Isle of Bute has followed a systematic trajectory from being a long‐standing popular holiday destination with attractive natural amenities, to a popular retirement destination with a developed recreational infrastructure and, latterly, a popular pre‐retirement destination in which personal networks influence migration decision‐making.