Prolonged instability and insufficiency of rainfall resulting in drought, extreme weather events, and food insecurity are climate change‐related challenges bedeviling humanity. This study assessed drought conditions and rainfall trends in southwestern Nigeria, using the 1984–2014 rainfall dataset from the Nigerian Meteorological Agency (NIMET). The coefficient of variation (CV), long‐term standardized precipitation index (SPI), serial correlation test, Mann–Kendall trend analysis, Sens's slope estimation, and Pettit test were carried out using various R programming packages. Long‐term mean annual rainfall ranged between 1224.7 and 1537.1 mm. The highest variation (17.3%) was observed for Abeokuta and Ikeja. SPI analysis revealed Ibadan and Oshogbo as the driest and wettest stations, respectively. There was no serial autocorrelation in the dataset. The Mann–Kendall trend showed an upward rainfall trend for Abeokuta, Ibadan, and Ikeja and a downward trend for Akure and Oshogbo. Sen's slope annual rates of change in mm for Abeokuta, Akure, Ibadan, Ikeja, and Oshogbo are 6.69, −2.36, 2.07, 7.82, and 1.42 respectively. The Pettit test revealed change points that are not statistically significant. The drought assessment largely showed a cyclical SPI pattern with greater years of dryness. Given the increasing impact of climate change, future studies are needed to simulate the local drivers of drought severity and frequency and the changing rainfall pattern in rapidly urbanizing cities. There is also the need to incorporate climate‐related adaptive strategies in existing water management policies.