This paper analyzes rainfall data to characterize the rainy season and define rice and maize crop calendars for current and future conditions in Madagascar. The daily rainfall data are taken from observational climate records and climate model simulations from the CMIP6 under the SSP245 and SSP585 scenarios. Rainy season characteristics are calibrated to fit rice and maize crop growth stages. The comparison between the past (1950–2018) and the future (2030–2100) highlights changes in the onset and cessation dates, which happen later and earlier, respectively. This causes the reduction of the rainy season duration, which affects the rice and maize crop calendars, especially its sowing or seeding periods. The worst (best) case is mainly observed in the southeast (southwest). On the one hand, the southwestern region may need to adapt to grow rice and maize crops with short or medium crop cycles in the future. In the Highland or Central land, the length of the sowing or seeding period increases. On the other hand, the North and East face a significant reduction in the length of the sowing or seeding period. Rice endures more than maize. Growing rice crops twice a year may not be possible in the future. But rather, we observe minor changes in the West. Our analysis suggests the imperative necessity to advise smallholder farmers to rely on short crop cycle varieties of rice and maize crops. Predominantly, the harvesting period is postponed. It is recommended to carefully consider our results for the definition of food policies.