Land-based transport corridors and their related infrastructure increasingly extend into and across the Arctic in support of resource development and population growth, causing large-scale cumulative changes in northern socio-ecological systems. These changes result from the increased mobility of people, goods and resources, and from environmental impacts on landscapes and ecosystems as the human footprint extends into remote, unindustrialized regions. Arctic climate change is bringing new challenges for construction and maintenance of transport systems, requiring adaptive engineering solutions as well as community resilience to change. In this review article, we consider the complex entanglements between humans, the environment and land transportation infrastructure in the North, and illustrate these aspects by way of seven case studies: 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 anticipated and built 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.