Although summer offers a natural context for adolescents to gain community-based work experience, little is known about the extent to which youth with disabilities are accessing these transition-related opportunities. We examined the summer employment experiences of 220 youth with high-incidence disabilities at two time points. Although more than half of all youth were employed at some point during the summer, youth with emotional/behavioral disorders and intellectual disabilities worked at significantly lower rates than youth with learning disabilities, and all received limited formal support related to finding and maintaining their jobs. Skill-related factors and spring work experience emerged as prominent predictors of summer employment outcomes. We present recommendations for schools, families, and communities to expand summer employment opportunities for youth with disabilities as an avenue for promoting career development. (Contains 6 tables and 1 figure.)