Low Impact Development (LID) is alternative design approach to land development that conserves and utilizes natural resources to minimize the potential negative environmental impacts of development, such as flooding. The Woodlands near Houston, Texas is one of the premier master-planned communities in the United States. Unlike in a typical urban development where riparian corridors are often replaced with concrete channels, pervious surfaces, vegetation, and natural drainage pathways were preserved as much as possible during development. In addition, a number of detention ponds were strategically located to manage runoff on site. This article uses a unique distributed hydrologic model, Vflo™, combined with historical (1974) and recent (2008 and 2009) rainfall events to evaluate the long-term effectiveness of The Woodlands natural drainage design as a stormwater management technique. This study analyzed the influence of LID in The Woodlands by comparing the hydrologic response of the watershed under undeveloped, developed, and highly urbanized conditions. The results show that The Woodlands drainage design successfully reflects predeveloped hydrologic conditions and produces peak flows two to three times lower than highly urbanized development. Furthermore, results indicate that the LID practices employed in The Woodlands successfully attenuate the peak flow from a 100-year design event, resulting in flows comparable to undeveloped hydrologic conditions.