Many communities are working to enhance the sustainability of their physical, economic, and social systems. While economic and physical systems are routinely measured (e.g., money and energy), psychological and behavioral elements of social systems (norms, attitudes, and individual behavior) are seldom tracked. The objective of this research was to evaluate a potentially scalable approach to measure the impact of sustainability initiatives on these variables in a community engaged in holistic sustainability programming. Online survey data were collected in 2012 (N = 155) and 2016 (N = 137), measuring pro-environmental thought and behavior in two towns in Ohio: Oberlin, a community engaged in holistic efforts to enhance environmental sustainability; and a similar community (Berea) used as a control. Survey links were distributed via recruitment letters mailed to randomly selected community residents from a purchased mailing list. We used two (town) by two (time) between subjects’ ANOVAs to evaluate whether Oberlin saw predicted increases in sustainable thought and behavior from 2012 to 2016, compared to the control community. Despite verifiable participation in and awareness of sustainability programs in Oberlin, our survey results did not provide strong evidence that programs resulted in the desired changes in attitudes, norms, and individual behaviors. Recycling attitudes and LED bulb installation were two exceptions. We conclude that assessing the psychological and behavioral dimensions of sustainability poses particular challenges. We encountered ceiling effects and inadequate statistical power. Possibly, norms and attitudes are not easily influenced even by a holistic community-wide effort.