Photon upconversion upon 1550 nm excitation is of high relevance for applications in the third biological excitation window, for photovoltaics beyond current limitations, and enables appealing options in the field of glass fiber telecommunications. Trivalent doped erbium ions (Er3+) are the material of choice for 1550 nm excited upconversion, however, they suffer from a low absorption cross‐section and a low brightness. Therefore, the ability of silicon metasurfaces to provide greatly enhanced electrical near‐fields is employed to enable efficient photon upconversion even at low external illumination conditions. Hexagonally shaped β‐NaYF4:Er3+ nanoparticles are placed on large‐area silicon metasurfaces designed to convert near‐infrared (1550 nm) to visible light. More than 2400‐fold enhanced photon upconversion luminescence is achieved by using this metasurface instead of a planar substrate. With the aid of optical simulations based on the finite‐element method, this result is attributed to the coupling of the excitation source with metasurface resonances at appropriate incident angles. Analysis of the excitation power density dependence of upconversion luminescence and red‐to‐green‐emission ratios enables the estimation of nanoscale near‐field enhancement on the metasurface. The findings permit the significant reduction of required external excitation intensities for photon upconversion of 1550 nm light, opening perspectives in biophotonics, telecommunication, and photovoltaics.