Because of the location and history of Taiwan in these three hundred years, Taiwanese have been forming their unique culture and artistic characteristics. This essay researched on some early native calligraphers as model characters such as Kang, Yan-Quan, Chen, Ding-Qi, and Li, Pu-Tong.They inherited the calligraphy tradition from their time each in late Ching-Dynasty, Japanese Colonial Times, and early KMT government in Taiwan. The uniqueness of Taiwanese calligraphy has been constructed by these Taiwanese pioneers. There are three main points in this essay. First,the author makes comments on the art essence of calligraphy and the features of the development of calligraphy in Taiwan. The author also analyzes the advantages and disadvantages factors of the development. Second, the author takes some later local calligraphers as representatives to analyze their inheritance from the pioneers. Third, the author proposes the theory basis of constructing subjectivity of Taiwan calligraphy. At last, the author reflects and proposes suggestions to the calligraphy education nowadays in Taiwan.