Walking has been demonstrated to improve health in people with diabetes and peripheral arterial disease. However, continuous walking can produce repeated stress on the plantar foot and cause a high risk of foot ulcers. In addition, a higher walking intensity (i.e., including different speeds and durations) will increase the risk. Therefore, quantifying the walking intensity is essential for rehabilitation interventions to indicate suitable walking exercise. This study proposed a machine learning model to classify the walking speed and duration using plantar region pressure images. A wearable plantar pressure measurement system was used to measure plantar pressures during walking. An Artificial Neural Network (ANN) was adopted to develop a model for walking intensity classification using different plantar region pressure images, including the first toe (T1), the first metatarsal head (M1), the second metatarsal head (M2), and the heel (HL). The classification consisted of three walking speeds (i.e., slow at 0.8 m/s, moderate at 1.6 m/s, and fast at 2.4 m/s) and two walking durations (i.e., 10 min and 20 min). Of the 12 participants, 10 participants (720 images) were randomly selected to train the classification model, and 2 participants (144 images) were utilized to evaluate the model performance. Experimental evaluation indicated that the ANN model effectively classified different walking speeds and durations based on the plantar region pressure images. Each plantar region pressure image (i.e., T1, M1, M2, and HL) generates different accuracies of the classification model. Higher performance was achieved when classifying walking speeds (0.8 m/s, 1.6 m/s, and 2.4 m/s) and 10 min walking duration in the T1 region, evidenced by an F1-score of 0.94. The dataset T1 could be an essential variable in machine learning to classify the walking intensity at different speeds and durations.