The classic brachistrochrone problem is standard material in intermediate mechanics. Many variations exist including some accessible to introductory students. While a quantitative solution isn't feasible in introductory classes, qualitative discussions can be very beneficial since kinematics, Newton's laws, energy conservation, and motion along curved trajectories all play a role. In this work, we describe an activity focusing on a qualitative understanding of the brachistochrone and examine the performance of freshmen, juniors, and graduate students. The activity can be downloaded at https://w3.physics.arizona.edu/undergrad/teaching-resources.