Rural, economically disadvantaged communities face a bigger challenge than urban communities in recruiting and retaining high school (HS) students in science, technology, engineering, and mathematics (STEM) because many of these students do not have access to high-quality STEM opportunities. In this article, we describe a mentoring program we developed as part of a larger New York State education grant. This program was implemented in a rural community to connect undergraduate STEM students with HS students to increase HS students’ interest in these fields. In this program, HS students visited colleges, explored their interests in STEM, and learned about opportunities available to them in college and beyond. Here, we share the challenges and the successful strategies in implementing a mentoring program in a rural, economically disadvantaged region. The ideas described in the article were designed so other educators can gain insight on how to set up successful mentoring programs to attract and retain students in the STEM pipeline.