Throughout the history, it is well-known that the ingress and the progress of Islam in Indonesia, especially in Java and Madura, were held almost without any tension and conflict. Even in the societies with some former belief systems such as Animism and Buddhism, Islam was easily accepted as a religion that brings peace within its teachings. During periods, Islam and local cultures perform a dialectical relationship and give rise to local variances of Islam, such as Javanese Islam, Madurese Islam, Sasak Islam, Sundanese Islam, etc. Those variances of Islam are the result of an acculturation process between Islam with the local cultures. In other word, this process is also called as “inculturation”. These local variances of Islam, further termed as the “cultural Islam” in this paper, have become a characteristics of Indonesian Islamic societies phenomenon which are different from Middle-East’s Islamic society and European Islamic society. This paper discusses about the Madurese Islam, one of these cultural Islam’s variances. Dialectical process between Islam and the local culture of Madura in turn generates a unique Madurese Islam, which is distinctive and esoteric. In its further developments, Islam and Madurese tradition are seen as unity and inseparatable, though people can still distinguish one another. This study seeks to uncover and expose the Islamic cultural dynamics that exist and grow in Madura: how big is the change that occurred, in which part, and what factors underlie these changes. This study provides benefit in enriching our scientific study about Indonesian cultural heritage, especially about the dialectical relationship between Islam and Madurese local culture.