Using as a point of departure the paradigmatic example of musical landscape – Felix Mendelssohn’s overture The Hebrides (Fingal’s Cave), Op. 26 – this chapter considers how the idea of landscape came to shape the composition and subsequent reception of numerous Romantic works. In addition to addressing the question of why so much of this music has been heard to evoke a sense of place, attention is given to the very act of contemplating landscape, both by composers and by the protagonists that often occupy their works. Particular attention is given to Beethoven, Schumann, Liszt, and Mahler, but the expansive view of musical Romanticism offered here encompasses the proto-programmatic genre of the characteristic symphony, as well as the music of a diverse array of twentieth- and twenty-first-century composers from Charles Ives to Jonathan Harvey, composers whose engagement with Romantic landscape tropes reveal the continued relevance of this rich tradition.