Distance Education, nowadays defined more as Open and Distance Learning, dates back to 1800s. Once considered as using non-traditional approaches and delivery methods compared to conventional campus-based education, distance education now has become a mainstream form of education increasing its popularity and use in the 21st century. Distance education has taken various forms and different definitions have been adopted depending on the age it has been developed. Technologies and pedagogies of the age along with the societal circumstances have influenced how distance education is viewed and practiced making way for different generations of distance education. Distinct concepts, pedagogies and practices for distance education have also emerged on the journey distance education has taken since the 19th century. For this reason, this article firstly provides a critical review of the definitions of distance education presenting a new definition reflecting the affordances of the digital age. Moreover, the distance education generations are presented with focus on the factors leading to the forming of these new generations. Concepts such as transactional distance and social presence and trends and practices such as OERs, MOOCs and learning analytics are also addressed. Furthermore, the role of culture in design, delivery and perception of distance education is discussed with focus on the future of distance education.