During the winter season, snowplowing has a significant effect on road users as it is critical to winter road maintenance and operations. The main goal of this study is to generate optimal routes for snowplowing trucks for efficient road maintenance. In addition to the conventional problem of reducing travel time and distance, this study also incorporates actual operational constraints, such as minimum maintenance standards and driver safety, to improve the overall efficiency of operations. To achieve the objectives, we first implemented the Chinese Postman Problem (CPP) to create Euler circuits from the initial routes and then identified the shortest paths by applying Dijkstra’s algorithm. Then, the Tabu search algorithm was chosen as a metaheuristic algorithm for the optimization process that finds near-optimal solutions by considering operational constraints for snowplow routes. Unsafe turning conditions and minimum maintenance standards were taken into account in the objective function defined for the optimization process. In simulations, the route obtained by our approach was compared to one with the application of CPP only in terms of travel distance, time, turning conditions, and road maintenance priority.