Skidding is one of the commonly used technical options to extract wood from felling to landing. As such, several studies have been carried out to evaluate its effectiveness in terms of economics, environmental impact, and ergonomics. Most ergonomic studies have addressed the exposure to noise and vibration, and less effort has been devoted towards the evaluation of the skidder operators’ working environment. To our knowledge, the exposure to variability in temperature and humidity has not yet been studied for skidding operations. This study aimed at evaluating the variability of such microclimate parameters and at comparing them to their counterparts recorded in the forest environment. Based on comparative datasets collected in November 2020, our results indicate that skidder operators might endure a significant variation in temperature and relative humidity during operations, which in turn may affect their health. Compared to the forest environment, the differences in temperature and relative humidity were evident, contrasting and occurred in short periods of time, as an effect of the skidding operations and mobility on increased distances and of a considerable altitudinal range. It is likely for such variability to also come from the work behavior of different operators. Given the results and the season in which the data was collected, as well as other constraints of the study, further studies should be carried out to separate the operation time from the rest and meal breaks, to evaluate the variability in microclimate throughout all seasons, to control the state of the cabin doors, and to solve the problem of control data mobility so as to accurately reflect the outdoor conditions for each location a skidder may work on during skidding operations.