Land-based transport corridors and related infrastructure are increasingly extending into and across the Arctic in support of resource development and population growth, causing large-scale cumulative changes to northern socio-ecological systems. These changes include the increased mobility of people, goods and resources, and environmental impacts on landscapes and ecosystems as the human footprint reaches remote, unindustrialized regions. Arctic climate change is also generating new challenges for the construction and maintenance of these transport systems, requiring adaptive engineering solutions as well as community resilience. In this review article, we consider the complex entanglements between humans, the environment, and land transportation infrastructure in the North and illustrate these interrelations by way of seven case studies: the Baikal–Amur Mainline, Bovanenkovo Railway, Alaska–Canada Highway, Inuvik–Tuktoyatuk Highway, Alaska Railroad, Hudson Bay Railway, and proposed railways on Baffin Island, Canada. As new infrastructure is built and anticipated across the circumpolar North, there is an urgent need for an integrated socio-ecological approach to impact assessment. This would include full consideration of Indigenous knowledge and concerns, collaboration with local communities and user groups in assessment, planning and monitoring, and evaluation of alternative engineering designs to contend with the impacts of climate change in the decades ahead.