Respiratory allergies triggered by pollen allergens represent a significant health concern to the Irish public. Up to now, Ireland has largely refrained from participating in long-term aerobiological studies. Recently, pollen monitoring has commenced in several sampling locations around Ireland. The first results of the pollen monitoring campaigns for Dublin (urban) and Carlow (rural) concerning the period 2017–2019 and 2018–2019, respectively, are presented herein. Additional unpublished pollen data from 1978–1980 and, 2010–2011 were also incorporated in creating the first pollen calendar for Dublin. During the monitoring period over 60 pollen types were identified with an average Annual Pollen Integral (APIn) of 32,217 Pollen × day/m3 for Dublin and 78,411 Pollen × day/m3 for Carlow. The most prevalent pollen types in Dublin were: Poaceae (32%), Urticaceae (29%), Cupressaceae/Taxaceae (11%), Betula (10%), Quercus (4%), Pinus (3%), Fraxinus (2%), Alnus (2%) and Platanus (1%). The predominant pollen types in Carlow were identified as Poaceae (70%), Urticaceae (12%), Betula (10%), Quercus (2%), Fraxinus (1%) and Pinus (1%). These prevalent pollen types increased in annual pollen concentration in both locations from 2018 to 2019 except for Fraxinus. Although higher pollen concentrations were observed for the Carlow (rural) site a greater variety of pollen types were identified for the Dublin (urban) site. The general annual trend in the pollen season began with the release of tree pollen in early spring, followed by the release of grass and herbaceous pollen which dominated the summer months with the annual pollen season coming to an end in October. This behaviour was illustrated for 21 different pollen types in the Dublin pollen calendar. The correlation between ambient pollen concentration and meteorological parameters was also examined and differed greatly depending on the location and study year. A striking feature was a substantial fraction of the recorded pollen sampled in Dublin did not correlate with the prevailing wind directions. However, using non-parametric wind regression, specific source regions could be determined such as Alnus originating from the Southeast, Betula originating from the East and Poaceae originating from the Southwest.