This article reports the results of a retrospective survey of participants in an exemplary transition program for college-bound youth with disabilities. The study compared how male and female participants perceived changes in themselves in the areas of academic skills, social skills, Internet skills, levels of preparation for college and employment, levels of awareness of career options, and personal characteristics during the course of their participation; values of program components; and impact of program participation on their lives. In accordance with conventional gender stereotypes, significantly more boys indicated initial interests and/or career goals in the fields of science, technology, engineering, and mathematics (STEM). Financial security was reported by significantly more males and pursuit of independent living by significantly more females when asked about their primary motivation for seeking employment. Females perceived significantly greater changes in themselves than did males during the course of their participation. Girls reported that, prior to program participation, they perceived fewer career options than boys; by the time of the survey, females perceived more career options than males. Research results are of particular relevance to the preparation of girls with disabilities for college and careers, particularly in fields where they have been underrepresented.