This research aims to understand how changing characteristics of surface conditions during winter influence the walking experience and convenience. For this purpose, we have observed and measured naturalistic walking behaviour (n = 1551) in terms of step lengths and step frequencies on various surface conditions typically associated with winter environments. The results show that step lengths are significantly reduced on snow- and ice-covered surfaces compared to asphalt. Step frequencies are significantly increased on ice compared to asphalt. These changes in walking behaviour are likely done to increase stability and reduce the risk of falling on slippery surfaces. However, a possible effect of these alterations in walking behaviour might be that energy consumption of walking is increased. This might increase exhaustion, be deemed less attractive, and likely reduces acceptable walking distances during winter. Improved winter operation can compensate for some of the negative effects.