Using the data of meteorological information reanalysis, a statistical analysis of dates of the main sudden stratospheric warmings observed in 1958–2014 has been performed and their inhomogeneous distribution in winter months with maximums in the beginning of January, from the end of January to the beginning of February, and in the end of February has been shown. To explain these regularities, a climatological analysis of variations in the amplitudes and vertical components of Eliassen–Palm fluxes created by large-scale planetary waves (PWs), as well as of zonal-mean winds and deviations of temperature from their winter-average values in high northern latitudes at heights of up to 50 km from the surface has been carried out using the 20-year (1995–2014) collection of daily meteorological information from the UK Met Office database. During the aforementioned intervals of observing more frequent sudden stratospheric warmings, climatological maximums of temperature perturbations, local minimums of eastward winds, and local maximums of the amplitude and Eliassen–Palm fluxes of PWs with a zonal wavenumber of 1 in the high-latitude northern stratosphere were found. Distinctions between atmospheric characteristics averaged over two last decades have been revealed.