Theoretically pulse wave velocity (PWV) is obtained by calculating the distance between two waveform probes divided by the time difference, and PWV ratio is used to assess the arterial stiffness gradient (SG) from proximal to distal. The aim was to investigate segmental upper-limb PWV (ulPWV) differences and the effects of hypertension and or aging on each ulPWV and SG. The study collected multi-waveform signals and conduction distances from 167 healthy individuals and 92 hypertensive patients. The results showed significant differences between ulPWVs (P < 0.001), with increased and then decreased vascular stiffness along the proximal transmission to the distal peripheral artery and then to the finger. Adjusted for age and sex, ulPWVs in hypertension exceeded that of healthy individuals, with significant differences between groups aged ≥ 50 years (P < 0.05). The hrPWV/rfPWV (heart-radial/radial-finger) was reduced in hypertension and differed significantly between the aged ≥ 50 years (P = 0.015); the ratio of baPWV (brachial-ankle) to ulPWV differed significantly between groups (P < 0.05). Hypertension affected the consistency of rfPWV with hfPWV (heart-finger). The findings suggest that segmented ulPWV is instrumental in providing stiffness corresponding to the physiological structure of the vessel. The superimposition of hypertension and or aging exacerbates peripheral arterial stiffness, as well as alteration in stiffness gradient.