Ground-penetrating radar (GPR) is a non-invasive technology that uses electromagnetic pulses for subsurface exploration. In the railroad sector, it is crucial to assessing soil layers and infrastructure, offering insights into soil stratification and geological features and aiding in identifying subsurface hazards. However, the automation of radargram analysis is impeded by the lack of ground truth—accurate real-world data used to validate machine learning models—thus affecting the deployment of advanced algorithms. This study focuses on generating high-quality simulated data to address the shortage of real-world data in the context of object detection along railroad tracks and presents a fully automated pipeline that includes data generation, algorithm training, and validation using real-world data. By doing so, it paves the way for significantly easing the future task of object detection algorithms in the railway sector. A simulation environment, including the digital twin of a GPR antenna, was developed for artificial data generation. The process involves pre- and post-processing techniques to transform the three-dimensional data from the multichannel GPR system into two-dimensional datasets. This ensures minimal information loss and suitability for established two-dimensional object detection algorithms like the well-known YOLO (You Only Look Once) framework. Validation involved real-world measurements on a track with predefined buried objects. The entire pipeline, encompassing data generation, processing, training, and application, was automated for efficient algorithm testing and implementation. Artificial data show promise for better performance with increased training. Future AI and sensor advancements will enhance subsurface exploration, contributing to safer and more reliable railroad operations.