Exaggerated blood pressure responses to aerobic and resistance exercise are associated with future cardiovascular disease. However, it remains unclear whether the excessive blood pressure responses induce these degenerative changes or are just an initial symptom of cardiovascular disease. The aim of this study was to test the hypothesis that exaggerated blood pressure responses to exercise and activities of daily living decrease vascular endothelial function and increase arterial stiffness. We investigated aortic pulse wave velocity (PWV, an index of arterial stiffness), blood pressure and heart rate at rest, during dynamic resistance (leg press) exercise and during 24-h ambulatory blood pressure monitoring (ABPM), one–repetition maximum of leg press exercise, maximal oxygen uptake and conventional cardiovascular risk factors such as serum cholesterol concentrations in 36 middle-aged and older individuals (mean age, 61.0 ± 1.3 years). Systolic blood pressure (SBP) during resistance exercise was correlated with aortic PWV, independent of resting SBP (partial r = 0.399). In the stepwise regression analysis, SBP during resistance exercise, age, body mass index, and 24-h ambulatory heart rate were used as significant predictors of aortic PWV, independent of other variables (R² = 0.722). Additionally, 24-h ambulatory SBP was correlated with SBP during resistance exercise (r = 0.513) and aortic PWV (r = 0.472). In conclusion, these results suggest that SBP during resistance exercise is an independent predictor of arterial stiffness. Repeated excessive rises in blood pressure during resistance exercise and activities of daily living may increase arterial stiffness.