For countries with coastlines, ports not only offered access to high seas and hence opportunities for development; but also served as important gateways for people fleeing or returning. “Port songs” was a genre of Taiwanese popular music with themes or backgrounds about the sea/harbor/port. This research traced the surge of port songs and compared their similarities and differences in pre- and post-WWII eras to shed light on the transformation of Taiwanese popular songs and to illustrate their intricate relationships with society, culture, economics, ethnic groups and history of Taiwan. Findings of this study are as follows. (1) The formation and transformation, opening and closing of ports were closely related to the pre-war politics of capitalism and militarism, as well as the post-war historical experiences including the 228 Incident and the imposition of martial law by the Kuomintang (KMT) Government. (2)Ports carried the collective memories and imaginations of people of a particular era. When writing, reading, listening or singing port songs, these memories and imaginations endowed Taiwanese in those days with both means and room for richer interpretations to be drawn and more metaphors to be made. Port songs, as a popular culture, thus contained allegories of the plight suffered by the people and initiatives for criticizing and denouncing the harsh reality they faced. (3) Under the impact of the 228 Incident, port songs written in the early 1950s reflected not only the socio-economic desolation experienced by the Taiwanese, but also portrayed vividly the anxiety and anguish against disparity in treatment received by the Taiwanese and the Mainlanders under the KMT Government, the suppressed urge for rebellion against such injustice and the subsequent low-esteem as second-class citizens. (4) Port songs written in the late 1950s featured the social context in which grass-root Taiwanese trapped in economic deprivation were forced to leave their homes for better opportunities elsewhere, and also reflected the feeling of exhaustion, both physical and mental, commonly shared by the people of that era. Incidentally, such context and feeling were consistent with the predicament and sentiment of the rural population in the early post-war era. The implementation of land reform policy forced the rural population to abandon their land and migrate to cities in search for livelihood and survival. (5) Although the destinations for these rural migrants were cities rather than ports, such spatial switch between cities and ports offered an opportunity for analogies and metaphors to be drawn. There existed a translational relationship between port songs and the reality. The widespread popularity of and hence the huge demand for Taiwanese port songs brought about the trend for Japanese productions to be adapted or ‘re-created’. Along with these adaptations, singing techniques of enka were embedded into the Taiwanese re-creations and eventually became a unique characteristic of Taiwanese popular songs, making them distinctive from their Mandarin counterparts. The transition from traditional music and pre-war pop music framework with songs featuring feminine, indoor, and feeble elements to post-war modern music with ‘port songs’ characterized by masculine, outdoor and robust qualities reflect directly or indirectly the shift of Taiwanese popular culture in dependence and resemblance from inland (the Mainland) to overseas (Japan).