The aim of this study is to try a cooperative study and practice on the Shikoku Pilgrimage (Henro) on the basis of connection of Naruto University of Education with high schools and junior high schools in the Shikoku region and to examine meanings of experiences of the pilgrimage in students at the university and secondary schools. Programs on the pilgrimage were conducted four times in 2008-2009 and about sixty students tried the pilgrimage in a group and walked over thirty kilometers including hilly parts for a couple of days. It is pointed out the following matters through this study. First, experiences of the pilgrimage in a group may have effects on awareness of self?affirmation and empathy in students. After the pilgrimage, the practices, which each participant tried to express their feelings and impressions on their own experiences of pilgrimages by means of Kanji and Kana characters written with a brush and sumi ink, were attempted. Characters written by them were, for example, those of meaning ‘friend’, ‘encounter’, ‘face’, ‘heart’, ‘love’, ‘kindness’, ‘warmth’, ‘harmony’, ‘challenge’, development’, ‘advance’, ‘effort’, ‘dream’. The result of the practices may show that sentiments in participants were cultivated partly. Second, it is a matter for teacher education for university students. The pilgrimage as the practice provided a good opportunity for university students becoming teachers to lead secondary school students and broaden their understanding about students. It became a chance for university students to develop their teaching skills and abilities in the field. Third, I note a meaning of the practice from a point of view of career ducation for secondary school students. With contacts among participants consisting of students in several ducation stages, high school students had chances to get practical information on university life from active niversity students directly and junior high school students got information on high school life from high school students. Through the collaborative practice with the university and secondary schools, students had more incentives for the advanced learning.