This article discusses the phenomenon of wandering in Russian culture, which was very typical and popular especially in the end of the 19-th century, but totally disappeared after the establishment of a strict passport’s regime during the Soviet Union. According to the classification made by A. Smirnova, who distinguishes two types of Russian wandering: voluntary and involuntary, this paper puts emphasis on the three subtypes within the first type: pilgrimage, foolishness for Christ and mind-wandering. This article presents an analysis of the cultural phenomenon of pilgrimage and foolishness for Christ (that refer to such behavior as abandoning house for a short or long time and taking a journey on foot for religious purposes), and mind-wandering (which refers to the confrontation between the motivational value of wandering with the motivational value of the everyday trivial activities), their peculiarities and reflections in Russian literature.