The prolonged situation of COVID-19 has caused complete chaos in our everyday life and had also an immense impact on the development of the youth in the school class transition to the college level. Thus, this study would qualitatively explore the meaning of college freshmen’s experiences of development during the school class transition period in the COVID-19 situation. To do so, in-depth interviews were held with seven college freshmen who went through the transition period at the time, and the data were analyzed step by step according to the descriptive phenomenological qualitative research method proposed by Giorgi (1985). As a result, 15 components and five categories of the research participants’ perceptions and experiences were vividly revealed. In particular, the categories included “The end of high school years suddenly mixed up due to the COVID-19 pandemic,” “The opportunity barely seized to grow the dream inside and outside the school due to the threat of the infectious disease,” “The college looking empty reached after going through the turmoil of disaster,” “The microsystem’s support that comforted the inevitably lonesome early year as a college student,” and “My mind that allowed myself to hold out the loose entry into adulthood.” In addition, these resulted in the central topic, “The adulthood opened by sprouting the dream in my way despite the school class transition entangled by anxiety.” Lastly, this study made suggestions for supporting the healthy and happy daily life of young adults living while cultivating development during the school class transition period to college in the COVID-19 situation.