As tractors mainly transit rural roads, drivers can suffer from harmful vibrations transmitted though their seats. Thus, the driving comfort in tractors with agricultural equipment should be evaluated. To investigate the effects of forward motion and front-wheel steering on the driving comfort of two-wheel-drive tractors with agricultural equipment, we establish a man–machine–road virtual prototype for simulations and validate it experimentally. First, a tractor that has suspended agricultural equipment and is operating at front-wheel steering angles of 0°, 12°, 24°, and 36° is driven on a random level-D road. Simultaneously, the vibration accelerations experienced by the driver are obtained along the X, Y, and Z axes with the coordinate system defined according to the ISO 2631-1 standard. The combined weighted root-mean-square (RMS) acceleration corresponding to the driver’s whole-body vibration increases from 0.205 to 0.909 m/s2 when increasing the steering angle. Then, considering the forward speed as the variable, the front-wheel steering angle is set at 30°, and the vibration accelerations experienced by the driver are obtained when the tractor travels at 4, 5, and 6 km/h on a random level-D road. The combined weighted RMS acceleration corresponding to the driver’s whole-body vibration increases from 0.68 to 1.03 m/s2 when increasing the speed. Therefore, we found that the velocity of a tractor should be reduced while steering, and excessively large front-wheel steering angles should be avoided to increase driving comfort.