We study the mechanical activation of spiropyran (SP) in a doubly cross-linked polyurethane elastomer. Besides chemical cross-linking, the elastomer comprises polytetrahydrofuran as soft segments and hydrogen-bonding 2-ureido-4-pyrimidone (UPy) as hard segments. The material shows two color changes because of the ring-opening reaction of SP to merocyanine (MC) at strained state and the isomerization about the methane bridge of MC at relaxed state. Increasing tensile strain rate leads to stiffer and stronger elastomer as well as earlier activation of SP. The activation point of SP to MC always coincides well with strain hardening of the stress elongation curves. We further use the two-color transitions of SP to study the fracture of the elastomer during crack propagation.