Aiming to analyze the site conditions of treeline trees at the highest elevations, we investigated 360 km of treelines in the Upper Valtellina, Italian Alps. We analyzed approximately five trees per km and determined the environmental factors limiting treeline elevation by distinguishing between geomorphologic constraints (mean elevation 2355 m), climatic constraints (2530 m), and human impacts (2335 m). Up to 82% of the 1814 analyzed treeline trees were influenced by geomorphological constraints, whereas human impacts influenced only 3% of the trees. Climatic treelines (15% of trees) were most common in the western sector. Moreover we analyzed the frequency distributions of elevation, slope, and aspect. Elevation was the most important variable that was also strongly associated with climatic treelines. The slope variable was more strongly associated with treelines limited by geomorphology than by climate. By reconstructing the altitudinal dynamics at the Mt. Confinale study site, we found rates of an ongoing treeline upward shift of up to 2.6 m/y in the period 2000–2009. Our results indicate that climatic conditions related to the ongoing air temperature rise in this region will likely enhance the treeline shift, especially at high elevations (>2400 m a.s.l.) and on non-extreme slopes (<45°).