Decision-makers for road and stormwater infrastructure across America are faced with numerous problems that require immediate action. These decision-makers are faced with an option when the time arises to consider alternatives for these infrastructure systems: abide to the status quo solution or attempt a different strategy. Typically, these stakeholders choose solutions that are built to be rebuilt. Roadways and stormwater infrastructure provide two examples of infrastructure that requires constant modification and addition. However, other solutions provide opportunities that go against traditional decision-making and provide an opportunity to transform the surrounding land. Road diets remove lanes instead of building more. Green infrastructure such as river daylighting relies on natural land systems to solve problems. Both solutions share the ability to solve their respective problems while also revitalizing, or transforming the land surrounding them. However, barriers are presented to these solutions, such as scope uncertainty and funding sources. Case study research of the Indianapolis Cultural Trail and the Lick Run Greenway reveals that collaborative planning, goal framing, and unique funding structures are a few examples of overcoming barriers to innovative infrastructure. / Master of Science / As roadways and stormwater infrastructure across America is placed in an increasingly precarious position, decision-makers are tasked with designing innovative solutions. Typically, the solutions that are drawn up have been used countless times over decades of research. However, in the face of an uncertain climate and population effects, old solutions are less able to solve newer, bigger problems. Innovative infrastructure can not only perform its traditional duties, but also act as an attractor to cities. Road diets, which are projects that remove vehicle lanes, and river daylighting, which are projects that unearth piped streams to collect stormwater, are two types of transformative infrastructure. This research utilizes case studies of both to understand their barriers and how to overcome these barriers. The barriers that were found include uncertainty in the scale of the project as well as how to procure funds for the project. To overcome these barriers, a few findings include active community planning through open forums as well as selectively framing information of the projects to highlight their benefits.