Over 40,000 road crossings in Maine are maintained by Maine Department of Transportation (MaineDOT) managers, emergency managers, natural resource planners, and municipalities. Resource managers need a way to quickly and comprehensively assess, during the planning stages of potential transportation-related projects, how ecological, hydrologic, and structural characteristics of bridges and culverts and their watersheds could adversely affect project schedules and budgets. Factors that are critical to evaluate and incorporate into overall assessments of project risk include basin, land-use, and climatic characteristics; vulnerability to specific events, such as floods; and complicating factors in the watershed, such as endangered species, evacuation routes, and historical sites. A Python script tool has been built for ArcGIS Pro as an automated screening tool that draws on existing geographic information system (GIS) data layers to identify potential risk factors and quantify risk scores for bridges and culverts. This tool can help resource managers quickly evaluate projects, during early planning, in terms of variables that may adversely affect schedules or budgets.