In order to determine drying shrinkage in early age cementitious paste and ITZ, prior to a calculation of shrinkage coefficient and further complex coupling, experimental methods at micro-level and numerical methods at meso-level are separately performed as the initial steps. Digital images of a small-size 1-mm thick cement paste specimen with an embedded obstacle as a concrete model are captured at different magnifications and analyzed in drying experiments with Environmental Scanning Electron Microscope (ESEM) and Vic-2D. The drying shrinkage shows the dependence on image magnification, chosen Area of Interest (AOI) and RH variations. Numerical moisture flow/ drying simulations by Lattice Gas Automata (LGA) show the difference in a moisture gradient depending on the heterogeneity of the LGA domain (population with smaller and/ or larger solids). Expected higher moisture gradient around larger solids is confirmed in the LGA simulations, which could be an initial sign of gaps/microcracks in real ITZ.