Abstract: Mechanization equipment has been confined to advancing agricultural modernization in China’s hilly and mountainous regions. In this study, a multidimensional and context-specific strategy was proposed to align with the distinct geographical, economic, and historical parameters in Chinese agriculture. Such a strategy was required for the historical evolution of agricultural development in China. Mechanization challenges were also integrated with the broader frameworks of the agricultural and national modernization. A systematic forward-thinking planning was grounded in the historical logic of the agricultural modernization, the industrial and technological challenges. The constraints were determined to hinder agricultural mechanization. The strategies and research priorities were proposed to advance agricultural mechanization. There was the macro-level decision-making on the actionable insights for the technological innovation. The results show that: 1) The agricultural mechanization was of strategic significance for the national food security and industry upgrading in the hilly and mountainous areas. However, major challenges remained in the natural constraints, technical adaptability, research and development strength, as well as financial support. 2) The agricultural modernization must follow its inherent and historical logic in the hilly and mountainous areas. There were four elements of the production, management, technology, and professional farmers coordinated in a manner. The high quality and efficient development were fully assessed for the comprehensive progress. 3) The natural, social, and economic conditions were restricted as well. Some suggestions were offered for the sustainable and healthy development of agricultural mechanization, including the top-level design and systematic planning, local and independent innovation, multi-factor coordination and orderly promotion, policy support, and responsibility implementation. 4) Agricultural mechanization and equipment should focus on the highly efficient and convenient transfer technology, lightweight and versatile power chassis, light and efficient mechanical operation, and production information. The finding can provide a strong reference to integrate the agricultural machinery, technical model, and service system.