<b><i>Background:</i></b> Chronic endurance exercise training elicits desirable physiological adaptations in the cardiovascular system. The volume of exercise training required to generate healthy adaptations is unclear. This study assessed the effects of differing exercise training levels on arterial stiffness, compliance, and autonomic function. <b><i>Methods:</i></b> Eighty healthy adults (38.5 ± 9.7 years; 44% female) defined as endurance-trained (ET, <i>n</i> = 29), normally active (NA, <i>n</i> = 27), or inactive (IN, <i>n</i> = 24) participated. Cardiovascular markers, including hemodynamics, large arterial compliance and small arterial compliance (LAC and SAC), carotid-femoral pulse wave velocity (PWV), and spontaneous baroreceptor sensitivity (BRS) were assessed. <b><i>Results:</i></b> ET showed significantly greater LAC values (21.4 ± 6.5) than NA (16.9 ± 2.5; <i>p</i> = 0.002) and IN (14.7 ± 3.2 mL × mm Hg × 10; <i>p</i> = 0.028). Values for SAC and BRS were significantly higher in ET than IN (<i>p</i> &#x3c; 0.001 and <i>p</i> = 0.028, respectively), but not NA. Compared to IN, PWV values for ET and NA were significantly lower (<i>p</i> &#x3c; 0.003). After adjusting for covariates (age, sex, and SBP), significant associations with cardiovascular fitness status were noted for all markers but BRS. <b><i>Conclusion:</i></b> Endurance exercise increases LAC likely due to high-volume training; however, lower volumes of physical activity may be sufficient to positively benefit vascular health overall.