This study estimates the impact of rainfall variation on livelihood in Mt. Kilimanjaro using the Ricardian approach to capture farmers’ adaptation strategies to cope with climate change risks. The data for the analysis were gathered from a random sample of over 200 households in 15 villages and precipitation from rainfall observation posts placed in each of the surveyed villages. The precipitation data provide information on the effect of moisture at critical months in the growing season. Due to prevalence of intercropping among local farmers, the present study develops a multivariate model that assumes endogeneity between crop yields. Doing so allows the study to capture adaptation strategies that smallholders use by diversifying farm portfolio. The results indicate that Mt. Kilimanjaro agriculture is vulnerable to precipitation variation. However, farm vulnerability is heterogeneous across space, crops and, months. Location varying inputs are responsible for substantial percentage of crop yield. The study found ambiguous evidence about the ability of irrigation usage to reduce crop vulnerability to precipitation variation, but suggests that proper cost benefit analysis ought to be done in order to measure the welfare value of irrigation. In terms of future food security, climate simulations reveal that by 2029, it will no longer be ideal to produce coffee in Mt. Kilimanjaro if precipitation annually decreases by a minimum rate of 2%. While maize production will also suffer severe production reduction, banana production will decrease but not in an alarming rate by 2029.