The manufacturing industry is characterized by challenges including global competitiveness, unpredictable market evolutions, lack of skills, and supply chain disruptions. To gain competitiveness, manufacturing Small-Medium Enterprises (SMEs) shall pursue Digital Transformation (DT) which enables significant benefits such as operational excellence and long-term business sustainability. However, SMEs usually struggle to successfully implement DT due to several impediments like lack of consistency between business strategy and digital plans, internal cultural resistance, and limited resources. Thus, the present research aims to develop a roadmapping methodology that supports manufacturing SMEs to define and implement a structured DT plan. The authors first investigate the SMEs-tailored existing tools, their role, and their limits through a systematic literature review: detailing existing Maturity Models (MMs) and digital roadmapping approaches and evaluating how they intertwined. Today, digital roadmapping methodologies neglect some SME’s barriers, appearing as too generic and more adequate for large companies. They do not provide pragmatic support to ensure the strategic alignment between digital initiatives and corporate goals, as well as they do not offer practical guidelines to select and prioritize actions. To fill this gap, the authors conjectured a roadmapping methodology tailored on SMEs’ challenges. Three maps are elaborated to determine market, business, and strategic targets, and to assess their consistency with the identified digital initiatives. Furthermore, a methodological approach is provided to support SMEs during the evaluation of effort and benefits. The methodology was validated through application cases involving Italian manufacturing SMEs.