Objectives: The objectives of this cross-sectional study were to investigate the fear level of kindergarten children in the general population during dental outreach in a familiar kindergarten setting, and to explore the factors associated with the dental fear of kindergarten children. Method: Consecutive sampling method was used to select kindergarten children aged 3 to 5 to participate in a questionnaire survey and an outreach service. A behavioural observation type of instrument for dental fear and anxiety assessment—Frankl Behaviour Rating Scale (FBRS)—was chosen to investigate the fear level of the children. Bivariate analyses between various factors and children’s dental fear and anxiety were carried out using Chi-square test. Results: A total of 498 children participated in this study. Almost half (46%) of the children have had caries experience, and the mean dmft score was 2.1 ± 3.4. The prevalence of dental caries was 32%, 43%, and 64% in the 3-, 4- and 5-year-olds, respectively. Only 4% of the children scored negatively for dental fear and anxiety (95% CI 2.3%–5.7%). Children at three years of age displayed more dental fear and anxiety than children of older ages, but the difference in dental fear and anxiety among the genders and caries status was not statistically significant. Most of the children (92%) brushed daily, but only 20% of them used toothpaste. Most (85%) of them had never visited the dentist, and over 70% of them were mainly taken care by their parents. High levels of positive and cooperative behaviour and low levels of fear were found in this population. No statistical significance was found between the child’s dental fear and any factors except age. Conclusion: Children generally displayed low fear or anxiety levels in a dental outreach consisting of a non-invasive oral examination and preventive treatment in a familiar kindergarten setting. Conducting regular outreach dental services to kindergartens by providing oral examination and simple remineralisation therapies could be a promising strategy to not only control childhood caries, but also manage and reduce dental fear and encourage long term dental attendance in line with the medical model.