The concept of “transalpine corridor” enhances the linear, valley-shaped topography of Valtellina which provides the perfect setting for both linear sport activities (such as hiking, cycling, running, skitouring etc.) and cultural routes lined with monuments and site experience opportunities. Combining new digital accessibility technologies and mobility heritage (e.g., the Bernina railway route and the Via dei Terrazzamenti), visitors in Valtellina can enjoy a renewed connection with the landscape, in coherence with the principles of sustainable tourism. The proposal of a Sport&Heritage Corridor across the Alps envisions an innovative integration between sport activities and heritage fruition, supported by a scenic train line and made possible by dedicated apps now widely accessible. It is conceived as a “slow” corridor, in complementary to the high-speed transalpine corridors. The Sport&Heritage Corridor can become the lasting legacy of the upcoming Olympics: a regional strategy for rebranding Valtellina as heart of the system Como Lake-Engadine, transalpine pole between Milan and Zurich.