This article extends the argument that scholarship on marriages and families provides invaluable insights into town-gown relationships. First, a four-square matrix constructed from the twin dimensions of effort and comfort levels is used to describe a typology of campus and community associations. Next the construction of the Optimal College Town Assessment (OCTA), a measure that contains items reflecting both the effort and comfort dimensions, is discussed. We offer an analysis of data from a pilot study utilizing the OCTA with a sample of 602 individuals employed in three communities surrounding the regional campus of a major university, with particular attention paid to variation as a function of distance from the campus. We include a discussion of the implications of the findings for assessment efforts targeting town-gown relationships.