Natural forests are considered a reservoir of great biological diversity constituting one of the most important ecosystems in Europe. Quercus study is essential to assess ecological conservation of forests, and also of economic importance for different industries. In addition, oak pollen can cause high sensitization rates of respiratory allergies in pollen-allergy sufferers. This study sought to know the pollen production of six oak species in the transitional area between the Eurosiberian and Mediterranean Bioclimatic Regions, and to assess the impact of climate change on airborne oak pollen concentrations. The study was conducted in Ourense (NW Spain) over the 1993–2019 period. A Lanzoni VPPS 2000 volumetric trap monitored airborne pollen. A pollen production study was carried out in ten trees randomly selected in several Quercus forest around the Ourense city. Oak pollen represented around 14% of annual total pollen registered in the atmosphere of Ourense, showing an increasing trend during the last decade. Pollen production of the six studied oak species follow the proportions 1:1:2:5:90:276 for Q. ilex, Q. faginea, Q. rubra, Q. suber, Q. pyrenaica, and Q. robur respectively. We detected a significant trend to the increase of the annual maximum temperature, whereas a decrease of the maximum and mean temperatures during three previous months to oak flowering. This could be related with the detected trend to a delay of the oak Main Pollen Season onset of 0.47 days per year. We also found significant trends to an increase of the annual pollen integral of 7.9% pollen grains per year, and the pollen peak concentration of 7.5% pollen grains per year. Quercus airborne pollen monitoring as well as the knowledge of the reproductive behavior of the main oak species, bring us an important support tool offering a promising bio-indicator to detect ecological variations induced by climate change.