Concrete railway sleepers in ballasted track are laid on ballast and subgrade supporting systems. Full contact between sleepers and ballast is typically assumed for analysis and design purposes. Often, voids and pockets in the sleeper/ballast contact interface form between sleepers and the ballast underneath that could cause problems to both the sleepers and the track system as a whole. The current paper investigates the effects of ballast voids and pockets on free vibration response characteristics of in situ railway concrete sleepers. Finite-element modelling was employed to develop a dynamic model of the railway track incorporating concrete sleepers. This model includes the dynamic interaction of sleepers and ballast as part of the free vibration analyses of the in situ railway concrete sleepers. Several patterns of voids and pockets underneath railway sleepers were studied. The emphasis was placed on partial and full interaction between sleepers and ballast. The information on the vertical vibration modes provides an important insight into the dynamic response of concrete railway sleepers in different void-and-pocket configurations.