Convective weather events pose a challenge to the burgeoning low altitude aviation industry. Small aircraft are sensitive to winds and precipitation, but the uncertainty associated with forecasting and the frequency with which impactful weather occurs require an active detect and response system. In this paper, we propose a dynamic, data-driven decision support system, with components of forecasting, realtime sensor observations, and route planning. We demonstrate our technology in the Dallas/Fort Worth metroplex, a large urban area with frequent thunderstorms which hosts the CASA Doppler radar network.