Objective: Previous studies have investigated medical students’ interest in family medicine, as well as their intentions to work in rural areas after taking part in community-based clinical clerkships. Community-based clerkships are designed to teach medical students community healthcare and to increase the number of physicians working in rural communities following their graduation. However, few studies have examined which clerkship experiences, specifically, enhance medical students’ positive perceptions on community healthcare. This study aimed to examine the association between experiential learning in community-based clerkships and students’ positive perceptions on community healthcare.Patients and Methods: From 2015 to 2017, we conducted a questionnaire survey of 290 final year medical students, before and after completion of their community-based clerkships. The survey asked the students about their perceptions (categorized into “Worthwhile” and “Confident”) of community healthcare and experiential learning during their clerkships. We assessed 13 medical learning areas involving healthcare, medical care, welfare, and nursing care practice. Multivariable logistic regression was used to evaluate the factors associated with positive student perceptions.Results: Of the 290 students, 265 (91.3%) completed both the pre- and post-questionnaires. Of these, 124 (46.8%) were female, 67 (25.2%) were from small towns (of <100,000 people), and 87 (32.8%) selected clinical clerkships within depopulated areas. A total of 205 (73.3%) students reported positive perceptions on community healthcare. There was a significant association discovered between students’ positive perceptions on community-based healthcare and them taking part in experiential learning in mobile medical services (43 [16.2%] students experienced mobile medical services—adjusted odds ratio 6.65, 95%, confidence intervals 1.67–26.4, p = 0.007).Conclusion: Medical students’ positive perceptions on community healthcare were discovered to be associated with them taking part in experiential learning in mobile medical services during their community-based clerkships.