Parkinson's disease (PD) is a common neurodegenerative disease presenting with both motor and non-motor symptoms. Among PD motor symptoms, gait impairments are common and evolve over time. PD motor symptoms severity can be evaluated using clinical scales such as the Movement Disorder Society Unified Parkinson's Rating Scale part III (MDS-UPDRS-III), which depend on the patient's status at the time of assessment and are limited by subjectivity. Objective quantification of motor symptoms (i.e. gait) with wearable technology paired with Deep Learning (DL) techniques could help assess motor severity. The aims of this study were to: (i) apply DL techniques to wearable-based gait data to estimate MDS-UPDRS-III scores; (ii) test the DL approach on longitudinal dataset to predict the progression of MDS-UPDRSIII scores. PD gait was measured in the laboratory, during a 2 minute continuous walk, with a sensor positioned on the lower back. A DL Convolutional Neural Network (CNN) was trained on 70 PD subjects (mean disease duration: 3.5 years), validated on 58 subjects (mean disease duration: 5 years) and tested on 46 subjects (mean disease duration: 6.5 years). Model performance was evaluated on longitudinal data by quantifying the association (Pearson correlation (r)), absolute agreement (Intraclass correlation (ICC)) and mean absolute error between the predicted and true MDS-UPDRS-III. Results showed that MDS-UPDRS-III scores predicted with the proposed model, strongly correlated (r=0.82) and had a good agreement (ICC(2,1)=0.76) with true values; the mean absolute error for the predicted MDS-UPDRS-III scores was 6.29 points. The results from this study are encouraging and show that a DL-CNN model trained on baseline wearable-based gait data could be used to assess PD motor severity after 3 years.Clinical Relevance-Gait assessed with wearable technology paired with DL-CNN can estimate PD motor symptom severity and progression to support clinical decision making.