Cultural heritage sites and landscapes are intuitively connected in urban systems. Based on available databases of cultural landmarks, we selected three pairs of cities that are currently dominated by three contrasting religions (Catholic, Buddhist and emerging culture) to compare the long-term changes in cultural landmarks, to quantify their spatial distribution in the current landscape, and to examine the potential influences these landmarks have on landscapes. The landmark database and landscapes were constructed from archived maps, satellite imagery and the UNESCO heritage sites for Barcelona, Bari, Beijing, Vientiane, Shenzhen, and Ulaanbaatar. Roads in Asian cities are mostly constructed in alignment with the four cardinal directions, forming a checkerboard-type landscape, whereas Bari and Barcelona in Europe have examples of roads radiating from major cultural landmarks. We found clear differences in the number of landmarks and surrounding landscape in these cities, supporting our hypothesis that current urban landscapes have been influenced similarly by cultural landmarks, although substantial differences exist among cities. Negative relationships between the number of cultural landmarks and major cover types were found, except with agricultural lands. Clearly, cultural landmarks need to be treated as “natural features” and considered as reference points in urban planning. Major efforts are needed to construct a global database before an overarching conclusion can be made for global cities.