Health monitoring, rehabilitation, and fitness are just a few domains where human activity recognition can be applied. In this study, a deep learning approach has been proposed to recognise ambulation and fitness activities from data collected by five participants using smart insoles. Smart insoles, consisting of pressure and inertial sensors, allowed for seamless data collection while minimising user discomfort, laying the baseline for the development of a monitoring and/or rehabilitation system for everyday life. The key objective has been to enhance the deep learning model performance through several techniques, including data segmentation with overlapping technique (2 s with 50% overlap), signal down-sampling by averaging contiguous samples, and a cost-sensitive re-weighting strategy for the loss function for handling the imbalanced dataset. The proposed solution achieved an Accuracy and F1-Score of 98.56% and 98.57%, respectively. The Sitting activities obtained the highest degree of recognition, closely followed by the Spinning Bike class, but fitness activities were recognised at a higher rate than ambulation activities. A comparative analysis was carried out both to determine the impact that pre-processing had on the proposed core architecture and to compare the proposed solution with existing state-of-the-art solutions. The results, in addition to demonstrating how deep learning solutions outperformed those of shallow machine learning, showed that in our solution the use of data pre-processing increased performance by about 2%, optimising the handling of the imbalanced dataset and allowing a relatively simple network to outperform more complex networks, reducing the computational impact required for such applications.