Approximately 500000 patients present with critical limb ischemia (CLI) each year in the U.S., requiring revascularization to avoid amputation. While peripheral arteries can be revascularized via minimally invasive procedures, 25% of cases with chronic total occlusions are unsuccessful due to inability to route the guidewire beyond the proximal occlusion. Improvements to guidewire navigation would lead to limb salvage in a greater number of patients. Integrating ultrasound imaging into the guidewire could enable direct visualization of routes for guidewire advancement. In order to navigate a robotically-steerable guidewire with integrated imaging beyond a chronic occlusion proximal to the symptomatic lesion for revascularization, acquired ultrasound images must be segmented to visualize the path for guidewire advancement. The first approach for automated segmentation of viable paths through occlusions in peripheral arteries is demonstrated in simulations and experimentally-acquired data with a forward-viewing, robotically-steered guidewire imaging system. B-mode ultrasound images formed via synthetic aperture focusing (SAF) were segmented using a supervised approach (U-net architecture). A total of 2500 simulated images were used to train the classifier to distinguish the vessel wall and occlusion from viable paths for guidewire advancement. First, the size of the synthetic aperture resulting in the highest classification performance was determined in simulations (90 test images) and compared with traditional classifiers (global thresholding, local adaptive thresholding, and hierarchical classification). Next, classification performance as a function of the diameter of the remaining lumen (0.5 to 1.5mm) in the partially-occluded artery was tested using both simulated (60 test images at each of 7 diameters) and experimental data sets. Experimental test data sets were acquired in four 3D-printed phantoms from human anatomy and six ex vivo porcine arteries. Accuracy of classifying the path through the artery was evaluated using microcomputed tomography of phantoms and ex vivo arteries as a ground truth for comparison. An aperture size of 3.8mm resulted in the best-performing classification based on sensitivity and Jaccard index, with a significant increase in Jaccard index (p<0.05) as aperture diameter increased. In comparing the performance of the supervised classifier and traditional classification strategies with simulated test data, sensitivity and F1 score for U-net were 0.95±0.02 and 0.96±0.01, respectively, compared to 0.83±0.03 and 0.41±0.13 for the best-performing conventional approach, hierarchical classification. In simulated test images, sensitivity (p<0.05) and Jaccard index both increased with increasing artery diameter (p<0.05). Classification of images acquired in artery phantoms with remaining lumen diameters ≥ 0.75mm resulted in accuracies>90%, while mean accuracy decreased to 82% when artery diameter decreased to 0.5mm. For testing in ex vivo arteries, average binary accuracy, F1 score, Jaccard index, and sensitivity each exceeded 0.9. Segmentation of ultrasound images of partially-occluded peripheral arteries acquired with a forward-viewing, robotically-steered guidewire system was demonstrated for the first-time using representation learning. This could represent a fast, accurate approach for guiding peripheral revascularization.