Little is known about college students during their summer break between the first and second years of college, when some students may contemplate whether they will return to college. Using ethnographic method, this article addresses critical questions of low-income college students during their summer breaks of where they go, where they stay, and what they do. Especially for the most vulnerable populations, unstable summer experiences have the potential to debilitate academic progress. Based on the literature of summer learning loss described as a concept when particularly low-income primary students experience a loss in core academic content, this study addresses its effects on college students. A setback or stagnant summer experience for low-income students during their first summer break from college could have the effect of accumulating academic and social loss with each passing year. Understanding what occurs outside of school sessions may help universities better prepare to support their students.