The Federal Motor Carrier Safety Administration (FMCSA) reported that commercial motor vehicles (CMVs), including large trucks and buses, comprised about 14% of total fatal crashes in the United States in 2018. Compared to other commercial vehicle types (e.g., taxis or commercial vans), CMVs require more driving skills and experience. Additionally, CMV drivers are more involved in long work hours, in-time delivery restrictions, and relatively inflexible working conditions. Despite the difficulties associated with long-haul CMV driving, very few studies have been documented to address driving challenges for long-haul CMV drivers. This study conducted a survey-based analysis to identify the concerns and difficulties encountered by long-haul CMV drivers in Kentucky. Questions encompassing different trucking aspects, such as drivers' socio-demographic characteristics, CMV-related factors, and work-specific features, were prepared. The survey was then posted online on the Kentucky Transportation Cabinet (KYTC) website and on KYTC's social media accounts, such as Facebook and Twitter. A total of 210 responses were gathered and used in the analysis. Comprehensive analysis was performed using descriptive statistics and graphical displays (such as pie/bar charts) and chi-square test of independence (to test the significant correlation between various factors vs. driver drowsiness/sleepiness and out-of-vehicle distraction). The results of the chi-square test showed that payment type, work flexibility status, presence of truck adaptive cruise control system, truck ownership status, nighttime driving, break taking, eating or drinking while driving, in-time delivery percentage, and listening to music/radio/podcasts when driving were significantly associated with the likelihood of driver drowsiness/sleepiness. Furthermore, respondents stated that lack of rest areas and parking spots, poor roadway maintenance, and lack of awareness/training for non-CMV drivers were the three main issues affecting long-haul trucking in Kentucky.