Ninety-six percent of the U.S. population lives in a county that has experienced a federally declared, weather-related disaster in the last several years. A major threat to coasts and rivers is development in flood-prone areas. Road-stream crossing infrastructure sized and designed for past land uses, and often focused on the single objective of directing water under roads, exacerbates this threat. Natural and nature-based infrastructure such as floodplains and road-stream crossings that allow fluvial connectivity can provide flood resilience, and direct water under roads, while also providing multiple additional benefits, including fish and wildlife habitat. This article investigates the statewide stream crossing design standard changes in Massachusetts that emphasize a multi-objective approach (traditional infrastructure integrity and ecological connectivity) to flood risk management. Four key categories of enabling conditions are identified that can help mainstream the use of nature-based approaches to climate resilience: regulations, technical assistance and funding, monitoring, and community engagement. This article investigates how these enabling conditions played out in Massachusetts to influence the statewide design of road-stream crossings.