To govern better future landscape planning of high-latitude agricultural systems, it is necessary to understand fully the drivers that currently determine farmers’ land allocation to different crops. The aim of this study was to identify key farm and field characteristics that drive farmers’ land allocation, based on substantial datasets, and to benchmark findings for farmer perceptions with interviews. Focus was on characteristics that are easily monitored and facilitate development of a field optimization tool to support future implementation and monitoring processes for land use changes at farm and field scales. Drivers for land allocation to different crops varied between crop production and dairy farms, but less evidently between southern and northern regions. Crop choices differed among regions, being greater for southern than for northern farms, but also for farm types, dairy farms mainly cultivating on-farm feed. Some special crops, such as potato and reed canary grass, represented diversified land use in the northern region, but farmers tended to allocate such crops very strictly to certain types of field and did not diversify crop rotations. Interviewed farmers highlighted the complexity of land allocation and the interactive nature of the drivers. When comparing outcomes of the data analyses and farmers’ interviews, field size, distance from farm center and soil type were considered to be primary drivers for land allocation. Field shape, slope and land ownership, but only in the case of long-term contract periods, were hidden drivers, identified using statistical analyses, but were not specifically referred to by farmers. Proximity to waterways was the only field characteristic classified as unimportant. Farmers highlighted logistical advantages as an important driver for land allocation, which was confirmed by data analyses. A farmer’s justification process for land allocation is likely to be based on intergenerational transitive knowledge and concepts of operationally critical farm and field characteristics. Valuable, empirical information gained during this study needs to be coupled with the development of policy measures to develop effective future policy instruments that are not only practicable, but are easily implemented and cost-effective, while remaining coherent with other policies.