The wine sector, among the most profitable agricultural segments, has been markedly affected by the ongoing climate change impacts, such as warmer climate conditions with higher frequency of extreme temperatures and a trend of decreasing precipitation. All this results in higher evaporative demand and therefore higher occurrence of water stress events leading to advancement of temperature-sensitive phenological stages (e.g., budburst and ripening). Such negative effects eventually affect berry development and quality, especially in historically valuable viticultural areas, forcing winegrowers to work within a compressed harvest period to maintain wine typicity. In this work we examined the relationship between environmental variables (air and soil temperature, relative humidity, precipitation, and solar radiation), phenology, berry, and wine quality for the two varieties (Chardonnay and Teroldego) in Trentino Alto-Adige/South Tyrol (Italy) over 36 years. Huglin Index (a bioclimatic heat index), growing degree days (measure of heat accumulation), and overall mean temperature showed linear increase (p < 0.001) in the last years, while no variations were recorded for precipitations. Despite no major effects being observed for phenological interval lengths, the onset of most of the phenological stages for both varieties had significantly (p < 0.001) advanced. However, i) early budburst pushed the budburst-flowering interphase by -1.2 days every two years toward putative colder periods with increased late frost probability and potential slower phenological progression towards flowering, and ii) early veraison shifted the veraison-ripening interphase by 0.25 day per year into warmer periods that oppositely impose faster phenological advancement. Hence, a substantial equilibrium in the seasonal growing length over years was maintained. Potential carry-over effects from the previous season were observed, particularly associated with heat requirements to unlock early phenological events, raising additional concerns on the additive effects of climate change to viticulture. Generally, white wine quality increased (p < 0.05) over the years, while red and sparkling wines remained unaffected. This was putatively related to accurate harvest date decision-making dictated by berry quality parameters: sugar-to-acidity ratio for Chardonnay and bunch sanitary status for Teroldego. Overall, this work provides evidence of the dynamics involved in climate change, and, to our knowledge, its overlooked effects on viticulture, thus providing new insights that can contribute to further developing adaptive strategies.