X-ray observations unveiled various types of radio-silent Isolated Neutron Stars (INSs), phenomenologically very diverse, e.g. the Myr old X-ray Dim INS (XDINSs) and the kyr old magnetars. Although their phenomenology is much diverse, the similar periods (P=2--10 s) and magnetic fields (~10^{14} G) suggest that XDINSs are evolved magnetars, possibly born from similar populations of supermassive stars. One way to test this hypothesis is to identify their parental star clusters by extrapolating backward the neutron star velocity vector in the Galactic potential. By using the information on the age and space velocity of the XDINS RX J1856.5-3754, we computed backwards its orbit in the Galactic potential and searched for its parental stellar cluster by means of a closest approach criterion. We found a very likely association with the Upper Scorpius OB association, for a neutron star age of 0.42+/-0.08 Myr, a radial velocity V_r^NS =67+/- 13$ km s^{-1}, and a present-time parallactic distance d_pi^NS = 123^{+11}_{-15} pc. Our result confirms that the true neutron star age is much lower than the spin-down age (tau_{sd}=3.8 Myrs), and is in good agreement with the cooling age, as computed within standard cooling scenarios. The mismatch between the spin-down and the dynamical/cooling age would require either an anomalously large breaking index (n~20) or a decaying magnetic field with initial value B_0 ~ 10^{14} G. Unfortunately, owing to the uncertainty on the age of the Upper Scorpius OB association and the masses of its members we cannot yet draw firm conclusions on the estimated mass of the RX J1856.5-3754 progenitor.