With the strong emergence of the bioeconomy in the US, there is growing interest in the ability of biomass production systems to meet the legislated demand for cellulosic biofuels. While corn grain will continue to comprise the primary feedstock for biofuel in the Cornbelt, it is unlikely that a single biomass feedstock will suit all the needs of an evolving bioenergy market; thus, the potential contribution of woody biomass should be considered. To meet informational needs, we conducted structured interviews with state-employed professional foresters along the Mississippi River corridor in five Corn Belt states (Illinois, Iowa, Minnesota, Missouri, and Wisconsin). Foresters were queried regarding the types of woody materials available, ecological considerations, the likely silvicultural systems that might support a biomass market, and their experiences with landowner management decisions as related to removing currently low-value material. Results suggest noteworthy interest in expanded woody biomass market systems within our study area. Furthermore, substantial opportunities exist to capture trimmings, small-diameter, and low-quality material in conjunction with on-going intermediate stand treatments or sawtimber harvests that are common in the region; capturing social and economic value while potentially contributing to long-term forest health. Costs for removing this material are estimated to range between $185–494/ha ($75–200/ac) depending on site conditions and accessibility. Such a wide range in costs (and therefore break-even biomass prices) suggests that some properties throughout the study region may be priced out of the market, at least in the initial stages of market development. Markets are distinctly lacking at present, however, and our interviewees suggested that market-pull will be required to organize a well-rounded infrastructure to harvest, process, store, and transport woody materials. This and future studies will be significant because they inform the enhancement of agricultural prosperity on small-to-medium farms and contribute to regional and national energy goals in ways that ideally improve, rather than diminish, the ecosystem services provided by woodlands in rowcrop-dominated landscapes.