Major advances in our understanding of the Universe have historically come from dramatic improvements in our ability to accurately measure astronomical quantities. The astrometric observations obtained by modern digital sky surveys are enabling unprecedentedly massive and robust studies of the kinematics of the Milky Way. For example, the astrometric data from the Sloan Digital Sky Survey (SDSS), together with half a century old astrometry from the Palomar Observatory Sky Survey (POSS), have enabled the construction of a catalog that includes absolute proper motions as accurate as 3 mas/year for about 20 million stars brighter than V=20, and for 80,000 spectroscopically confirmed quasars which provide exquisite error assessment. We discuss here several ongoing studies of Milky Way kinematics based on this catalog. The upcoming next-generation surveys will maintain this revolutionary progress. For example, we show using realistic simulations that the Large Synoptic Survey Telescope (LSST) will measure proper motions accurate to 1 mas/year to a limit 4 magnitude fainter than possible with SDSS and POSS catalogs, or with the Gaia survey. LSST will also obtain geometric parallaxes with accuracy similar to Gaia's at its faint end (0.3 mas at V=20), and extend them to V=24 with an accuracy of 3 mas. We discuss the impact that these LSST measurements will have on studies of the Milky Way kinematics, and potential synergies with the Gaia survey.