This multi-case study sought to better understand how students with intellectual disability (ID) are forging pathways to higher education via the community college. Five individuals with ID who accessed higher education via the community college and their parents/guardians were interviewed. Each case provided insight into personal pathways with results given in case descriptions and individual case themes. Cross-case analysis revealed four themes positively impacting the college-going pathway for students with ID: value-driven grit, pathway knowledge, community support, and accessibility. Based on findings from this study, families appear to be the primary systems forging pathways to the community college for individuals with ID. Local education agencies and community colleges can assist these families by engaging in interagency collaboration, evaluating their systems, and aligning practices to the goal of students with ID accessing and engaging in higher education.