This paper experimentally and numerically investigates the water hammer phenomenon in serially connected steel and HDPE pipes with different diameters. The aim of the laboratory tests was to obtain the time history of the pressure head at the downstream end of the pipeline system. Transient tests were conducted on seven different pipeline system configurations. The experimental results show that despite the significantly smaller diameter of the HDPE pipe compared to the steel pipe, introducing an HDPE section makes it possible to suppress the valve-induced pressure surge. By referring to the results of the experimental tests conducted, the comparative numerical calculations were performed using the fixed-grid method of characteristics. To reproduce pressure wave attenuation in a steel pipe, Brunone-Vitkovský instant acceleration-based model of unsteady friction was used. To include the viscoelastic behavior of the HDPE pipe wall, the one-element Kelvin–Voigt model was applied. By calibrating the unsteady friction coefficient and creep parameters, satisfactory agreement between the calculated and observed data was obtained. The calibrated values of parameters for a single experimental test were introduced in a numerical model to simulate the remaining water hammer runs. It was demonstrated that using the same unsteady friction coefficient and creep parameters in slightly different configurations of pipe lengths can be effective. However, this approach fails to reliably reproduce the pressure oscillations in pipeline systems with sections of significantly different lengths.