This project is a practical theological response to the so-called "rise of fundamentalism" and its extreme inverse—uncritical progressivism—in contemporary Orthodoxy within the United States. The dissertation argues that it is possible, and even traditional, for contemporary Orthodox communities to shape their religious practices in a manner that addresses fundamental needs in the present, without relying or insisting upon contextually inappropriate practices. Drawing on the so-called Christian practices approach to practical theology as found in the writings of Dorothy Bass and Craig Dykstra and the theology, spirituality, and mysticism of the Christian East—as exemplified by the writings of Maximus the Confessor—this project cultivates four critical lenses that contemporary Orthodox Christian communities can employ as they begin to explore the possibility of adapting traditional practices and incorporating innovative practices into their existing way of life. In order to concretize such an endeavor, this project includes a case study of the Communities at New Skete. In their own unique way, they have adapted their monastic life to meet their 20th and 21st century circumstances. Notably, they have engaged in a reform and renewal of the inherited liturgical tradition to meet not only their own needs, but also those of the Orthodox Church here in the United States. Additionally, and more significantly, they have allowed other spontaneously-arising activities to shape their way of life. For this latter point, the project focuses on the way that their dog breeding and training program has functionally become a spiritual practice for the monks and nuns. Their example can help contemporary Orthodox Christian communities consider the ways in which activities, which arise naturally in their own contexts, similarly function as spiritual or religious practices. In doing so, these communities can cultivate a contextually appropriate Orthodoxy, without falling into the trap of fundamentalist thought. This project will contribute to ongoing conversations around Christian practices, and to research at the intersection of practical theology and spirituality studies.