Human society as a whole has a reached a tipping point in its relationship with the socio-ecological systems upon which it depends. All sectors of society need to be involved in addressing this crucial challenge through a raised awareness of the issues and pro-active solutions to it. This research focuses on small urban towns and cities, where half the world’s urban population lives, and looks at the ways in which local government in these key areas can play an active role in leading sustainability through education and training. Municipalities and communities that use the framework for strategic sustainable development (FSSD) were investigated, and the conditions were identified that helped and hindered training to be really effective. Effective training, in its many forms, was found to be essential in fomenting a common language of sustainability, engaging the community, and bringing concerted strategic actions that together could foster a culture of sustainability.