Studies indicate that learners' participation in outdoor activities is limited in most pre-schools and emphasis put in academic oriented activity subjects. Some studies have sought to find out factors that inhibit learners' involvement in outdoor activities but pre-primary teachers' dilemma in implementing of learners psychomotor or outdoor activities has been given limited attention. The purpose of this study therefore sought to establish school factors that create a dilemma in implementing learners' outdoor activities in Hamisi Sub-County, Vihiga County, Kenya. The study adopted a mixed methods research design. Maria Montessori's theory of children' play was used for the study. A sample of 33 ECDE lead teachers, 27 ECDE teacher trainers and 12 learners from a target population of 110 ECDE lead teachers, 27 ECDE teacher trainers and 4400 learners was selected. Stratified proportionate sampling, simple random, purposive and census techniques were utilized to select the sample size. A questionnaire, interview schedule and observation guide were the instruments to collect data. A pilot study was conducted from the neighbouring Sabatia Sub County to ascertain the strength of the reliability and validity of the instruments. Validity was ensured based on construct and content validity. Reliability was ensured through test-retest technique. A reliability coefficient of 0.7 using Cronbach's Alpha Coefficient was attained for both instruments and therefore deemed appropriate for use in the actual study. The study enhanced ethical considerations. Qualitative data was analysed using content analysis. Quantitative data was analyzed using descriptive statistics such as frequencies, and percentages and findings presented in pie charts, bar graphs and tables. Inferential statistics ANOVA was used to establish the relationship between independent and dependent variable at 0.05 confidence level. The results showed that there was a significant difference in the means of the different school factors influencing the implementation of outdoor play activities in the curriculum {F (6, 25) = 2.840, p = .000}. The study concluded that pre-schools government policies like funding by parents, employment of qualified and professionally trained teachers by the county government and provision of minimum land size of ECDE centers enhance learners' performance in outdoor play activities. The study recommended the ECDE center managers to improve on provision of learners outdoor play activity facilities and materials like merry-go-round, slides, swings, climbing frames and teeters. This study was conducted in public pre-primary schools but a similar study should be carried out in private pre-primary schools.