Load carriage is an inevitable daily task for soldiers. The purposes of this study were to explore the extent to which gait variability (GV) is affected by load carriage and experience among military cadets, and whether experience-related differences in GV are dependent on task demand. Two groups of cadets (30 experienced, 30 less experienced) completed a load carriage task in each of three load conditions (no load, 16 kg, 32 kg). Three categories of GV measures were obtained: spatiotemporal variability, joint kinematic variability, and Lyapunov exponents. Compared to traditional mean gait measures, GV measures were more discriminative of experience: although both groups showed similar mean gait measures, the experienced participants had reduced variability in spatiotemporal measures (p ≤ 0.008) and joint kinematics (p ≤ 0.004), as well as lower levels of long-term local dynamic stability at the ankle (p = 0.040). In both groups, heavier loads were also caused increased GV (p ≤ 0.018) and enhanced short-term local dynamic stability at the knee (p = 0.014). These results emphasize the importance of GV measures, which may provide a more complete description of adaptability, stability, and control; highlight alternate movement strategies during more difficult load carriage; and capture experience-related differences in load carriage strategies.