This report focuses on the GoVermont program – a state managed rideshare matching program – as a window into the obstacles and opportunities to increasing carpooling in Vermont. In this project, researchers conducted an initial survey of 370 GoVermont participants and then conducted four in-depth conversations with 25 of those respondents. Researchers also reviewed GoVermont materials, previous research on carpooling and examined data from the US Census and NHTS data on travel behavior at the individual and household level. Findings indicate the difficulty in expanding carpool activities in the context of present settlement patterns, job distributions and car ownership. Regardless the results should be instructive to policy-makers seeking to improve car occupancy rates