The pressure distribution under the crossties plays a key role in railroad performance. This study conducts laboratory testing to investigate the pressure distributions under two different types of crossties, steel and timber. For each type, this study employs only a single tie. Five pressure cells are placed equidistantly under the rail crosstie between the two rails to measure the pressure distribution. Both static and cyclic loadings are applied during the test. The pressure distributions are compared between the steel and timber crossties. The effect of the cyclic loading on the pressure distribution also is explored. It is found that pressure distribution is different for steel and timber crossties. Cyclic loading could change the pressure distribution under both steel and timber crossties, but the effect of cyclic loading is more obvious on the steel crosstie than on the timber crosstie. Differences exist in pressure distribution between loading and unloading processes.