|Within the academy, it has been commonly acknowledged that Taiwanese Poetry Societies as a whole underwent major changes during the Japanese Colonial Period. However, what were these changes in reality? And what kind of social atmosphere do they reflect? What are their historic significance? Although these issues have long been discussed by scholars, there is ample room for in-depth investigation as well as exploration of these changes and careful observation of single cases. The ＂Island-wide Congress of Poets＂ (1924-1937), as a prominent annual event that took place for thirteen successive years without fail, was hosted by major poetry societies across the island. Members of these societies replicated each others’ successful experiences while serving as important sources of inspiration for local poetic organizations. This article sees the Congress as a prime opportunity all the scholars working on this phenomenon to do deeper analysis of the dynamics of influential poetic events: from their preparation, session processes, and subsequent activities. For more in-depth analysis, we use the specific congress held in Chiayi in 1934, which as the 20th Congress of Poets is marked for its historic significance. By closely studying it, we can better understand the event’s origins, influence, organization and participants. The changes of the way the Congress was structured would reflect the Congress’s response to modernization in terms of its utilization of systematic division of work in administrative regions, its historic impact, modern printing technology, and the railway. Meanwhile, we are to understand that despite being under colonial rule, Taiwanese poetry societies differed greatly in their organizational structure and social influence. In essence, they were nevertheless within the range of what Yen kun-yang proposes as a ＂Social culturality of Poetry.＂ Even more so, with the help of modernization, Taiwanese poets attempted to spread poetry into every social corner. Though their effort was thwarted in 1937 by Japanization, as a cultural event fighting against governmental authority, it was remarkable for its cultural as well as historical values.