This study is to explore the current status and obstacles facing Taiwan high school principles participating in recreational sports. A total of 499 high school principals in Taiwan and its surrounding islands have been included in this study. A self-designed instrument, "Questionnaire of High School Principals'." The questionnaire consisted of three parts: personal information, recreational sports survey, and its obstacle. As a result, out of 499 school principals surveyed, 387 completed and returned their questionnaires, out of 387 returned questionnaires, only 373, or 74.75% were counted as being valid. Based upon the purpose and the hypotheses testing of this study. All data were processed using descriptive statistics, item analysis, factor analysis, T-test One-way ANOVA. The following are two major findings: In terms of the high school principals' seniority and where their schools were located, there were significant differences found with the interpersonal and social obstacles they encountered when participating in their recreational sports. In conclusion, the recommendations proposed by this study will be offered to Taiwan sports and recreation authorities for their reference.