We studied a method of quantitatively evaluating safety levels by train operational control in gale conditions. For the purpose of the evaluation, we estimated the functions of distribution of wind velocity occurrence and wind temporal fluctuations. Using these functions, we calculated the probability of a gale occurring in a given section during train operation. The authors compared the calculated probability with the relative frequency observed at the site. A model section for wind velocity observation was assumed, and several different train operation methods were compared with the safety level evaluation of each method in the section by calculating the probability.