Decision support capabilities that provide flightspecific reroutes around constraints can enable more flexible and agile management of the airspace. For this benefit to be realized, automation must reliably provide operationally-acceptable alternatives to traffic managers. This paper proposes an approach for generating a small number of diverse, feasible solutions for further evaluation by traffic managers. Using a variation on Dijkstra's shortest path algorithm, reroutes are designed for one or more flights, where multi-flight problems promote the active design of reroute flows. A multi-objective genetic algorithm is employed to evaluate trade-offs between multiple criteria of operational acceptability, removing the need to pre-define relative metric weightings. Finally, a combination of Principal Components Analysis and Spectral Clustering is used to identify distinct groups of solutions and representative reroutes that capture different trade-offs between metrics of operational acceptability. Results are generated for a historical convective weather event and evaluated for their characterization of the trade-space.