The transportation industry employs a wide range of workers, from truck drivers to construction workers operating in active traffic zones. Workers are constantly exposed to unfavorable temperatures that affect their physical and mental health, making it important for them to have longer and more frequent rest periods to recover. Therefore, the objective of this study is to investigate the various factors that contribute to the need for longer breaks when working in cold temperatures. To achieve this objective, a comprehensive questionnaire survey was developed and distributed online to workers in the construction industry. Total responses gathered from the survey distribution were 100 responses. The survey data was used to develop a predictive logistic regression model. The results revealed that dexterity, ineffective cold protective clothing, and the lack of a sufficient cold protection plan are significant indicators that contribute to the need for workers for longer breaks. However, other factors, such as worker age, gender, fatigue, and mental stress, were not significant enough to contribute to the need for extended breaks. The results also indicated that reduced exposure to cold weather with sufficient protective clothing can help in improving their performance in cold temperatures. The outcomes from this study will help employers in construction industry to develop an efficient cold weather work-rest regime, as they understand the various health challenges construction workers experience in cold temperatures, as well as the factors that contribute to their need for extended recovery periods.