Abstract: Operations in cold regions require vehicular maneuvering across snowpacks or frozen surfaces. Winter roads and their route determination, construction, and monitoring are widely studied. This report analyzes historical and current literature on winter road construction and operations, reviews risk assessment techniques, examines the impact of uncertain weather on road reliability, and provides a standard operating procedure for design, maintenance, and use. Winter roads, snow roads, ice roads, and ice bridges enable seasonal access in Arctic and Subarctic regions. They allow cross-country maneuverability over terrain like wetlands and bogs, which are impassable in summer. These roads are critical for training, logistics, and construction in areas without all-season access. When combined with ice bridges they can provide near-unlimited travel. Effectiveness depends on proper planning, construction, and monitoring. Snow roads require controlled compaction for strength, while ice roads require sufficient ice thickness to support loads. Both rely on tools like visual inspections, ground-penetrating radar, and unmanned aerial systems to ensure safety. With extreme seasonal variability, adaptive strategies are essential. Shortened seasons and unpredictable freeze–thaw cycles demand modern technologies, predictive weather modeling, and improved reinforcement. This report integrates historical knowledge with engineering advancements to improve winter road durability, reduce risks, and support cold-region operations.