In this paper, I read Mark Twain`s Following the Equator (1897) focusing on his transitional stance on imperialism. Although he is known as a strong anti-imperialist compared to other intellectuals and politicians of the period, it was not clear about exactly when he started criticizing Western imperialism. In regard to Twain`s stance against Western imperialism, I argue that his last global lecture tour (for the purpose of paying off his debts) changed his perspective, particularly after he observed the reality of the colonized in India. Clemens initially expected to be released from the complexities of modern American society and to return to an “innocent” human condition in the Third World. While he was traveling to the major cities of the British Empire such as Sidney, Bombay, Calcutta, and Cape Town, however, Clemens experienced the repercussions of imperialism that were molded by the imperial regimes and modern technologies. For example, migrating from one city to another for book readings or lectures let Mark Twain encounter diverse populations (from Western travelers who abuse native Indians, to a widowed Indian woman who is buried following an Indian tradition of sati). These varied experiences in colonial India, I argue, made him change his perspective on Western imperialism abroad. His strong criticism against the Philippine-American War and American intervention in China in the early twentieth century thus presents his changed perspective on Western imperialism.