Whenever bicyclists ride on public roads, they ride through roadway defects which occasionally causes them to lose control of their bicycles and/or damage components. Previous research has quantified the forces experienced during general road and offroad riding, but did not study the specific influences of variables such as pothole geometry, riding speed, etc. To begin quantifying these effects, a road bike was equipped with a triaxial accelerometer and ridden over poor roadway conditions around an industrial park in Southern California. Next, in a laboratory setting, an artificial pothole was constructed that was 12 inches long and either 1 or 1.65 inches deep. A force plate was placed at the far edge to measure the horizontal loads induced by the bicycle tire riding over the edge and high-speed camera was positioned perpendicular to the path of travel to measure the speed and vertical drop of the front wheel. Lastly, two riders of differing weights rode the same road bicycle over the artificial pothole at target speeds of 8, 10, and 12 mph. As anticipated, vertical wheel drop and impulse duration were inversely correlated to speed, and peak horizontal force was strongly correlated with vertical wheel drop, which resulted in an inverse correlation between peak force and speed for tests in which the wheel did not contact the bottom of the pothole. The data was then used to validate analytical functions derived to calculate vertical drop, impulse, and peak force from horizontal speed, pothole geometry, and bicycle-rider characteristics. This study lays the foundation for additional testing with varied conditions (more riders, different pothole geometries, wider tires, etc.) to expand the analytical model to apply to a more general set of conditions.