Abstract: Planning, designing, constructing, and maintaining all-season roads in cold regions requires navigating complex environmental, hydrologic, and geomorphologic challenges. Harsh conditions, such as permafrost, frost-susceptible soils, muskeg, and extreme cold, are compounded by limited data availability, remote locations, and fragile ecosystems. Recent Arctic strategies across the DoD have identified changing weather patterns as significant threats to infrastructure, operations, and training land management in these regions. Key risks include degrading permafrost, changes in precipitation intensity and duration, and the loss of soil bearing capacity in saturated soils, all of which are examined in detail. As the Department of Defense expands Arctic training capabilities, infrastructure investments across Alaska must balance operational goals with sustainability and resilience. This report synthesizes the military’s typical methods for constructing roads in contingency environments, identifies practices used in the construction of the Alaska-Canada Highway, and draws from consultations with training land managers, a thorough literature review, and active engineering research. The report highlights the importance of holistic design that prioritizes longevity, environmental conservation, and safety by addressing cold-region challenges, mitigation strategies, and best practices. This resource is indispensable for military units and infrastructure planners tasked with navigating the complexities of cold-region infrastructure construction and operation.