When there are railway tunnels on both sides of a valley, a bridge is usually built to let trains pass. However, if the valley is very close to an urban area, building an open-cut tunnel at the portal and then backfilling it to create available land resources for the city and to prevent excavation slag from polluting the environment would be a wise choice. This has led to the emergence of a new type of structure, namely, the high-fill open-cut tunnel. In this paper, by performing an automatic long-term field test on the first high-fill open-cut tunnel using a bilayer design in China, the variations of earth pressure and structural internal force during the backfilling process were obtained, and different tunnel foundation types were studied. The results showed that the earth pressure significantly exceeded the soil column weight, with a maximum earth pressure coefficient between 1.341 and 2.278. During the backfilling process, the earth pressure coefficient increased at first and then decreased slowly to a relatively stable value, and a stiffer foundation would make the structure bear higher earth pressure (1.69 times the normal one observed during monitoring). The change of internal force had two stages during backfilling: before the backfill soil reached the arch crown, the internal force of the lining changed slowly and then grew linearly as the backfill process continued. Moreover, the axial force ratio of the inner and outer linings was close to their thickness proportion, and the interaction mode between the two layers was very similar to the composite beam.