A gust factor, defined as the ratio between a peak wind gust and mean wind speed over a period of time, can be used along with other statistics to examine the structure of the wind. Gust factors are heavily dependent on upstream terrain conditions (roughness), but are also affected by transitional flow regimes (specifically, changes in terrain and the distance from the upstream terrain change to the measuring device), anemometer height, stability of the boundary layer, and, potentially, the presence of deep convection. Previous studies have yielded conflicting results regarding differences in gust factors that might exist between winds generated by tropical cyclones and those generated by extratropical systems. Using high-resolution wind speed data collected from both landfalling tropical cyclones and extratropical systems, two databases of wind characteristics were developed. Gust factors from tropical cyclone and extratropical winds were examined, summarized, and compared. Further analysis was conducted to examine and compare the characteristics of the associated tropical and extratropical wind speed histograms. As expected, the mean gust factor was found to increase with increasing upstream surface roughness. Some differences were observed between data from the tropical environment and the extratropical environment. Mean gust factors from the tropical regime were found to be higher than mean gust factors from the extratropical environment within each roughness regime and the wind speed histograms generated from data from the two environments indicated some differences.