College students with disabilities continue to experience various challenges in their transition into postsecondary education. However, limited research has focused on their initial transition, despite the significance of its impact on college students with disabilities. This qualitative study examined first-semester transition experiences among freshmen with disabilities at a public research university in the Southeastern United States. Responses (i.e., post-course interviews, course reflections, online discussion boards) from thirteen students of 2018 to 2021 cohorts of the Engage 100 course (an orientation program for freshmen with disabilities) were analyzed through a qualitative analysis approach. The results indicated that college freshmen benefit in their social and academic transition through enrolling in the Engage 100 course. The results highlight the need for disability support services and for college campuses to foster transition success for college students with disabilities.