We report on two quantitative, morphological estimators of the filamentary structure of the Cosmic Web, the so-called global and local skeletons. The first, based on a global study of the matter density gradient flow, allows us to study the connectivity between a density peak and its surroundings, with direct relevance to the anisotropic accretion via cold flows on galactic halos. From the second, based on a local constraint equation involving the derivatives of the field, we can derive predictions for powerful statistics, such as the differential length and the relative saddle to extrema counts of the Cosmic web as a function of density threshold (with application to percolation of structures and connectivity), as well as a theoretical framework to study their cosmic evolution through the onset of gravity-induced non-linearities.