AbstractCharacterizing soil moisture around drip irrigation pipes is crucial for precise and optimized farming. Machine learning (ML) approaches are particularly suitable for this task as they can reduce uncertainties caused by soil conditions and the drip pipe positions, using features extracted from relevant datasets. This letter addresses local moisture detection in the vicinity of dripping pipes using a portable microwave imaging system. The employed ML approach is fed with two dimensional images generated using back projection as a radar‐based algorithm and the Born approximation as an inverse scattering method, based on spatio‐temporal (collected data at various positions over the soil surface and at different time points.) measurements at various frequencies. The study investigates the performance of K‐nearest neighbour (KNN) and convolutional neural networks (CNN) algorithms for moisture classification based on these imaging techniques. We also explore the potential of KNN and CNN for moisture estimation around the plant roots and in the presence of pebbles. In general, CNN outperforms KNN in moisture content detection from microwave data, especially after applying imaging algorithms. A combination of CNN as the ML approach and the back projection algorithm to provide training data, yielded accuracy more than other models for moisture content estimation. Also, the practical results demonstrate that our method can detect soil moisture with an estimation error of less than 10%.