Land cover mapping has been a valuable tool in capturing changes in many developing regions in Africa. Senegal has been a hotspot of change where agricultural activity has rapidly increased. Agriculture in this region is often a complex mosaic of small fields which makes them difficult to classify using conventional land cover mapping methods and coarse-resolution satellite imagery. WorldView (WV) satellites provide very high-resolution imagery that is ideal for semantic segmentation using convolutional neural networks (CNN). In this study, we introduced training strategies that scale up the training data for the U-Net model using 2 m WV-2 and 3 imagery to overcome the challenges of regional mapping with a patchwork of hundreds of images. The proposed strategies increased the number of training data for the U-Net model in three main scenarios, (i) conventional training, (ii) model transfer, and (iii) transfer learning, and we evaluated model generalizability on test sets for two different regions in Senegal. The results showed that models rapidly reached a high level of performance with a limited increase in additional training in conventional and transfer learning strategies. In these two strategies, the U-Net consistently produced >87% average accuracy for trained images and >70% average accuracy for all test images at the final scale level. The research opens opportunities to produce regional land cover maps in West Africa without generating a prohibitively large amount of training data.