The purpose of this study is to explore not only the principles and aims of education, but also the concepts and principles of happiness in ancient Asian wisdom, especially Indian and Chinese classics as well as religious sutras. In order to investigate this article systematically, three research questions are addressed: First, what are educational principles and aims of the Upanishads and the Brahma-Sutras vs. the Analects and the Mencius? Second, what are happiness concepts and principles of Bhagavad Gita vs. Tao Te Ching? Last, what are significant similarities and differences of education and happiness appeared in ancient Indian and Chinese classics? To defend the above three research questions, the researcher utilizes a descriptive content analysis method, with a cross cultural approach. One of findings of this study is: the Gita provides happiness concepts spiritual, religious, and pragmatic, while the Tao Te Ching offers happiness ones naturalistic, ethical, and metaphysical. Based on the research results of the study, the author suggests that the principles and concepts of happiness as well as the principles and aims of education may seem to impart the useful resources and valuable theories of happiness or well-being education to contemporary educational practitioners and theorists in order to establish the sound morals of individuals, societies, and nations. For future research, it is recommended that the study be broadly undertaken to investigate the merits of educational, philosophical, and religious thought in the classics of both worlds.