Automated pavement distresses detection using road images remains a challenging topic in the computer vision research community. Recent developments in deep learning has led to considerable research activity directed towards improving the efficacy of automated pavement distress identification and rating. Deep learning models require a large ground truth data set, which is often not readily available in the case of pavements. In this study, a labeled dataset approach is introduced as a first step towards a more robust, easy-to-deploy pavement condition assessment system. The technique is termed herein as the Pavement Image Dataset (PID) method. The dataset consists of images captured from two camera views of an identical pavement segment, i.e., a wide-view and a top-down view. The wide-view images were used to classify the distresses and to train the deep learning frameworks, while the top-down view images allowed calculation of distress density, which will be used in future studies aimed at automated pavement rating. For the wide view group dataset, 7,237 images were manually annotated and distresses classified into nine categories. Images were extracted using the Google Application Programming Interface (API), selecting street-view images using a python-based code developed for this project. The new dataset was evaluated using two mainstream deep learning frameworks: You Only Look Once (YOLO v2) and Faster Region Convolution Neural Network (Faster R-CNN). Accuracy scores using the F1 index were found to be 0.84 for YOLOv2 and 0.65 for the Faster R-CNN model runs; both quite acceptable considering the convenience of utilizing Google maps images.