The transition to secondary school from the accustomed environment of primary school was found to have several challenges being met by most of the grade seven students. The study aimed to explore the experiences of the students and sought to identify important issues and challenges they face. Using the descriptive phenomenological design, the researchers uncovered and described the experiences of 17 purposively sampled participants. Data from a semi-structured interview, observation, focus group discussions, and a journal was gathered during the first three weeks as Grade 7 students enter secondary school for the first time. The results from this study obtained 5 major themes: students experience different milieu of relationships; inferiority complex due to bullying and unruly classmates; school location, and other different barriers that are beyond student’s control. Study shows that the experience could be enjoyable for some and could be problematic to others if not given enough understanding and support. It is recommended that school administrators look into the experiences of the students and provide programs for a smoother transition process.