Literary sources from the late Second Temple period provide an intriguing window into developing conceptions of the Sabbath as it moves from its biblical roots to its construction in the Tannaitic period. Key authors, including Philo, Josephus and the editors of the documents found at Qumran, each brought specific worldviews to bear in their literary creations about the Sabbath which shaped both the form and content of their writings. Philo took a philosophical view of the mitzvot (commandments of the Torah) with an eye toward their role in improving human character. Josephus looks at Sabbath observance through the prism of history indicating how it influenced Jewish life and impacted Jewish history during the Second Temple period. Finally, the community at Qumran took special interest in developing the observance of the Sabbath through the creation of halakhah that would define the practices appropriate to that day. This paper takes a comparative approach to the distinct vantage points that each of these parties took in their writings on the Sabbath, with particular emphasis on how these texts shape our understanding of the ongoing development of the Sabbath in late antiquity.