INTRODUCTION: OpenStreetMap (OSM) road surface data is critical for navigation, infrastructure monitoring, and urban planning but is often incomplete or inconsistent. This study addresses the need for automated validation and classification of road surfaces by leveraging high-resolution aerial imagery and deep learning techniques. METHODS: We propose a MaskCNN-based deep learning model enhanced with attention mechanisms and a hierarchical loss function to classify road surfaces into four types: asphalt, concrete, gravel, and dirt. The model uses NAIP (National Agriculture Imagery Program) aerial imagery aligned with OSM labels. Preprocessing includes georeferencing, data augmentation, label cleaning, and class balancing. The architecture comprises a ResNet-50 encoder with squeeze-and-excitation blocks and a U-Net-style decoder with spatial attention. Evaluation metrics include accuracy, mIoU, precision, recall, and F1-score. RESULTS: The proposed model achieved an overall accuracy of 92.3% and a mean Intersection over Union (mIoU) of 83.7%, outperforming baseline models such as SVM (81.2% accuracy), Random Forest (83.7%), and standard U-Net (89.6%). Class-wise performance showed high precision and recall even for challenging surface types like gravel and dirt. Comparative evaluations against state-of-the-art models (COANet, SA-UNet, MMFFNet) also confirmed superior performance. DISCUSSION: The results demonstrate that combining NAIP imagery with attention-guided CNN architectures and hierarchical loss functions significantly improves road surface classification. The model is robust across varied terrains and visual conditions and shows potential for real-world applications such as OSM data enhancement, infrastructure analysis, and autonomous navigation. Limitations include label noise in OSM and class imbalance, which can be addressed through future work involving semi-supervised learning and multimodal data integration.