A robust supply chain is critical to ensure a sustainable supply of feedstock to the existing and emerging bioenergy and bioproducts industries. Logging contractors are a key group in this process, since they provide harvesting and transportation services, and their success is directly linked to innovation activities. Surprisingly, very little is known about the innovation system in the logging industry—especially about how it relates to biomass supply. Failure to understand how logging contractors adopt and implement biomass production technologies could lead to failed innovation efforts, unmet development goals, and a lack of properly equipped contractors. This article presents results from a series of case studies of highly innovative logging contractors in Maine. All of the firms had some experience producing biomass within their operations. The firms had also used multiple biomass harvesting technologies. This study highlights the variation in challenges that led to the adoption (or rejection) of biomass as a product innovation—with particular emphasis on harvesting technologies. A major finding of this study was the need for a high degree of collaboration between landowners, logging contractors, and biomass consuming facilities in the innovation process. The future development of the biomass industry is highly dependent on contractors adopting biomass harvesting and related technologies. The innovation process of logging firms is an area that is not sufficiently studied, and this research provides valuable insight into this important component of the forest biomass industry.