The goal of this study is to examine how high school students' curricular and extracurricular decisions translate both into college enrollment and into college retention. We estimate a dynamic discrete choice model in the spirit of Keane and Wolpin (1997) and Rust (1987) to capture the sequential nature of curricular decisions. Rich individual-level panel data are provided by ACT that follow high school students from the end of 8th grade biannually through high school graduation and up to college enrollment and retention. At each point in time in- dividuals make decisions of their high school course work and the extracurricular activities in which they participate based on past enrollment decisions, on grades and on measures of academic achievement. Using maximum likelihood we recover structural estimates of the model's parameters and, treating high school curriculum and extracurricular activities as an investment in human capital, we determine the rate of return on this investment. We relate this investment to two college outcomes: enrollment and retention. Finally, we investigate how decisions made throughout high-school a ect both the probability of entering college and the probability of staying in college.