To inscribe the Grand Canal on the World Heritage List is facing challenges in the search and designation of its heritage meanings. Dominated by the Western-originated Authorized Heritage Discourse (AHD), efforts in giving meanings to the material remains of the canal failed in making sense of its fundamental cultural value. How the ancient Chinese spoke of and understood the Grand Canal in Confucian classical discourse are glossed over by globalized expressions such as tangible/intangible heritage, linear heritage or man-made water project, etc. In this paper, we attempt to rethink the value, representations, and meanings of the Great Canal as Chinese waterway cultural heritage beyond the manipulation of AHD. We turn to Zhou Dao, the road system of Zhou Dynasty (1046-256 BC), addressing how the ancient meanings as recorded in varied classical texts about this road system may shed light on the meaning-making of the Grand Canal in the present socio-political contexts. Firstly, Zhou Dao was not merely channels of communication or systems of transportation, but also and more importantly a ritual nexus that connected the sage-kings with their people in the kingdoms. It reflected the art of political governance through exemplifying virtues to educate the populace, and could be considered a ritual space of Dezhen (benevolent governance). This cultural significance of Zhou Dao may be helpful for us to reinterpret the Grand Canal beyond a means of communication. The earliest section of the canal Hangou constructed by the lord of the Wu State during 722-481 BC, was aimed at establishing the ritual order of Zhou Dynasty. In later generation, both Emperor Kangxi and Emperor Qianlong regarded their travel along the Grand Canal as a way of examining the custom and cultures of the people and practicing the ritual politics following the ideal sage-kings. This political vision was expressed by a poetic description of Zhou Dao in the Confucian The Book of Songs, both physically and spiritually depicted as the following: ″The way to Zhou is level like a whetstone, And straight as an arrow. The officers tread it, And the lower people see it.″ Secondly, underlying the construction of Zhou Dao, a unique Chinese way of conceptualizing space was at work, i.e., an understanding of the governance from the center of goodness to the four directions (Sifang Guan). Through the road system, the Dao and virtue embodied in the sage-kings symbolically flows from the center to the peripheral, from the sage-kings to the people. The ritual governance across the whole nation was materialized through its waterway as well as its road systems. From this cultural perspective of geopolitics, the meanings of the Grand Canal may need to be reinterpreted from Confucian ritual perspective of fostering qin (love) among the kings and the people. Emperor Yu's taming of the flood, which can be seen as the precursor of canal making and the moral access to the benevolent government of Wang Dao. Through Wufu, the five circles of love, around the kings, both geographically and culturally, the virtue-based spatial governance of the Grand Canal is constructed. With this ritual centre for people to respect, to follow and to be attracted toward, both Zhou Dao and the Grand Canal functioned to establish spiritual bonds within the four seas, based upon love and benevolence. Thirdly, the transmitting and remaking the meanings of the Zhou Dao across thousands of years deserves special attention in its uses of the past. The term Zhou Dao is derived from The Book of Songs. Through generations of diverse interpretation, annotation and edition of the Confucian heritage as text, Zhou Dao, operating as the source of meanings, transmitted the Way of Antiquity to inspire people how to manage and use waterway or road systems. From the endless interpretation of Confucian Orthodox, new meanings can spring and illuminate the present predicaments. As a result, the recordations of the Grand Canal scattered in divergent Confucian Classics, historical records, philosophical writings and other miscellaneous works. Understanding the indigenous meanings of the Grand Canal should not only rely on the factual interpretation of these recordations, but also the employment and inheritance of the Confucian Orthodox, which is a heritage practice by means of harnessing the past to create the future. With the interpretation of Zhou Dao in The Book of Songs, Yu Gong in The Book of History, and Hangou in The Commentary of Zuo, we seek to get the indigenous insights of the Grand Canal heritage in the perspective of Confucian Classics, and also expand the humanistic concern of Zhou Dao and the Grand Canal to the management of modern traffic and logistic systems. The paper is significant in that it stimulates us to dig deeply into the cultural meanings of Chinese heritage through careful studies of ancient texts so as to make the past relevant and reviving in the use of heritage today.