A rollator, one of the most widely used among walking assistance devices, can assist the elderly with stable walking in their daily lives. In this study, we investigated how the structural characteristics of two types of rollators affect the upper and lower extremity muscle activity and plantar pressure of the elderly in various walking environments. We quantified muscle activity (upper and lower limbs) and plantar pressure (mean force, peak pressure, and contact area) of 11 older adults walking in various environments (flat, obstacle, uneven, and sloped terrain) using two types of rollators. Upper extremity muscle activity was highest in the obstacle terrain and the uneven terrain, and a significant difference was found due to the structural differences of the rollator. Additionally, it was observed that lower extremity muscle activity and plantar pressure patterns appeared in accordance with the gait strategy to maintain stability in an unstable or inclined walking environment. In other words, it was confirmed that the weight of the rollator, the size of the wheel, grip type, and the auxiliary tools had a great effect on the upper and lower extremity muscle activity and plantar pressure of the elderly during walking. From the results of this study, it can be suggested that it is absolutely necessary to consider the biomechanical characteristics of the elderly and the structure of the rollator, which appear differently depending on the walking environment, in the development of walking aids. In the future, more clinical data will be collected, and based on this a rollator that can safely assist the elderly in various walking environments will be developed.