AbstractMechanochromic polymers can be used as stress‐ and damage‐detecting sensors in polymeric materials, given that mechanical stimuli can be visualized by color changes. Although many types of mechanochromic polymers have been reported so far, there are only few examples on their further functionalization based on multiple color changes (multicolor mechanochromism). Herein, preliminary results are reported on the use of multicolor mechanochromism to detect the duration of the mechanical stimulation by simply mixing white powders of two mechanochromic polystyrene samples that contain a different radical‐type mechanochromophore at the midpoint of each polymer chain and thus exhibit different colors in response to mechanical stimuli. The mechanosensitivity can be tuned via the polymer length and shape, and a combination of these two types of mechanochromic polymers allows detecting the duration with multicolor mechanochromism, i.e., a color change from white to blue upon short exposure to grinding and a color change from white to gray upon longer exposure to grinding. Electron paramagnetic resonance and solid‐state UV–vis measurements support the mechanism proposed for this multiple mechanochromism.