The fast transmission of signals around the globe is fundamental to the flow of information for our society. A long-haul transmission certainly represents one of the key advancements that shaped modern ways of communicating and offers a nearly instant access to any available data or a latest information. However, fiber-optic transmission typically suffers from a variety of physical impairments that degrade the signal quality, thus imposing limits on both, the achievable transmission capacity and data reach. Of particular concerns are stochastic fiber impairments, primarily represented by polarization mode dispersion (PMD). The PMD originates from a random birefringence caused by imperfect fiber circularity and other, both internal and external, effects, basically completely re-defining the light polarization state of output signal compared to its initial counterpart. The PMD is particularly critical as it restricts operation of fiber-optic links running at speeds higher than 10 Gbps. This, in turn, hinders fiber link re-adaption towards higher transmission bit rates in future, however. In this context, both in-line link monitoring and testing of PMD-based effects is of great importance within the recently used optical fiber links. However, polarization-based effects are also very sensitive to the environmental changes, substantially degrading transmitted optical signals and reducing link quality. In this work, we provide experimental characterization for PMD-based propagation effects in optical fibers influenced by wind gusts. The investigation was performed on commercially used fiber-optic link that runs through optical power ground wire cables. The 111-km-long optical link under study comprised installed optical fibers with available 88 channels. Here, we monitored environmental changes caused by wind conditions over several consecutive days with a 60 second time frame and sensed PMD impact on the link performance. Here, differential group delay (DGD) was chosen to be a key parameter, enabling for sensitive characterization of wind related link changes. Measured maximum DGD’s were 4 and 10 ps for wind speeds up to 5 and 20 m/s, respectively. In addition, experimentally measured data were used in numerical model to assess the optical link quality. For a low wind condition, we observed negligible quality degradation in the optical link, considering transmission bit rates of 10, 40, and 100 Gbps. Conversely, in case of strong wind condition, the optical link maintained a reliable operation only for established 10 Gbps, while significant link degradation was observed for bit rates of 40 and 100 Gbps. Our work shows promising way to effectively sense and monitor undesired environmental variations and their impact on polarization-based fiber link propagation effects, which in turn, can allow an instant link quality evaluation.