The Vermont Community Foundation's (VCF) 2009 report on postsecondary education asserts that college graduates live longer, healthier, more lucrative lives than their peers who did not graduate college. But the report is harsh in its assessment of the readiness of Vermont high school students for college. Vermont's expenditures for high school students are among the highest in the nation, yet these students lag in college preparation. These are troubling data about the possibilities for Vermont youth to achieve the goals of college graduates. Given the need for a bachelor's degree for many future jobs, improvement in collegiate graduation rates could not be more important. Nevertheless, if there are weaknesses in college preparedness among Vermont high school students, which the VCF report suggests, and if these weaknesses are exacerbated by misaligned and non-rigorous curricula, then Vermont's first-generation students will struggle mightily if and when they progress to college. At Southern Vermont College (SVC), more than 60% of the students are the first in their families to progress to a bachelor's degree. This article describes the support provided by SVC to its students and presents concrete examples of SVC's new initiatives. In addition to these initiatives, the mini-mester program offers high school students a brief, intensive, on-campus academic and residential life experience that has a career focus and opportunities for students to try out their navigational skills in a safe, caring and controlled environment. This program will be especially beneficial for those who are the first in their families to consider a four-year residential collegiate opportunity. To extend the idea of partnering using the mini-mester idea, SVC and Wheelock College are collaborating to pilot a one-credit mini-mester this summer geared towards high school juniors from both urban and rural settings. It will provide these students a unique opportunity to learn about and engage in hands-on experiences related to health care, with problem-based learning that demonstrates the difference between urban and rural health care delivery systems. Partnering is one way, in addition to SVC's current on-campus efforts, to help more Vermonters succeed in higher education. The stakes are high, but the rewards for students and the larger community are clear: longer-living, healthier, wiser, more engaged citizens. The very future of the state depends upon the success of such partnering initiatives.