The ongoing fragmentation of ash populations due to ash dieback requires an effective gene flow between individuals; thus, investigations on ash pollen transport are essential. In this study, comprehensive aerobiological field experiments at two seed plantations in Baden-Württemberg were conducted in 2019 and 2020 in order to study the influence of phenology and meteorology (especially wind) on pollen transport using self-constructed gravimetric pollen traps located 1.5 and 5 m a.g.l. Our main objectives were to investigate the local scale dispersion of ash pollen and to evaluate the recommended distance (i.e., 400 m) from seed plantations to other ash trees according to the German Forest Reproduction Act. Our results showed a link between pollen transport and meteorology, the onset of phenological development, and the topography of the plantation. The plantation at Schorndorf was characterized by a slope and associated cold air flows, suggesting that this could be a factor contributing to higher pollen levels at the downslope traps. In addition, in many cases, the cardinal direction associated with the highest pollen impaction was also identical with the predominant wind direction. Analyzing pollen data for single traps in detail, we found that the highest total pollen catch (31%) was measured outside the plantations in 2019, a year with very low flower development. In contrast, most pollen (33%) was caught within the plantation in 2020, which presented a much stronger pollen year than 2019 (with a factor of 11 regarding total sums). This indicates, in the lower pollen year, a potential higher contribution of trees from outside the plantation, and thus it can be recommended that seed harvesting of ash trees in the plantations should preferentially take place in full mast years. Interestingly, the total pollen deposition in Emmendingen at 5 m height showed little difference compared to the traps at 1.5 m height, but there was a large temporal difference pointing to vertical variations in pollen availability. In general, we found that ash pollen was transported for a larger distance than 400 m, but the amount of pollen decreased substantially with increasing distance. At a distance of 200 m, there was already approx. 50% less pollen captured from the air. However, even at a distance of 500 m, more than 10% of the pollen was still captured. In order to ensure cross-pollination of healthy ash trees, the distance of ash individuals or stands should not be too large, and there should be no spatial separation (e.g., by conifer stands).