The texture of fresh tomatoes (Lycopersicum esculentum Mill., ‘Momotaro’) at three different stage of ripeness (mature green, pink, and red) was intensively evaluated. The double-cycle load plate compression test showed that initial firmness, average firmness, energy absorption, deformation ratio, and relaxation ratio were sensitive textural parameters for identifying the maturity stages. From a puncture test, initial firmness, average firmness, apparent modulus of elasticity, rupture force, toughness, and deformation at the rupture point were sensitive to the maturity stages. The mature unripe tomato deformed linearly as a function of force; hence, the firmness was constant. However, the fully ripe tomato firmness increased as a function of applied force. The fruit strain increased during ripening, and it was independent of fruit size. The unripe tomato was more elastic than the ripe one. The peel at the mature green stage contributed approximately 70% of the firmness of the fruit and approximately 90% at the pink stage and red stage. The rupture force by the puncture test (traditionally, peak force) was correlated well with other textural parameters, which indicated that it could be used as a firmness representative parameter, as has been used by many researchers. The degree of elasticity was a better indicator for elasticity than the relaxation ratio.