Skagway, gateway to the Yukon. Is this pretty or is this pretty? 10/20/05: Few have agreed on how this town should be spelled, or what the name means. Originally a Tlingit word, it has been variously spelled Skaguay, Schkague, Shkagway, Skague, Schkawai and even Cquque. Most suggest that it means "home of the north wind" but others say it means "spirit of the cruel wind", "end of the salt water", or "rough water". Still others, using supposedly authentic sources, suggest it means "lady relieving herself on a rock" or "sound a sled runner makes when it breaks loose from the snow and ice." The town erupted from a homestead to a full-size city during the winter of 1897-98, witnessed the building of the railroad from 1898-1900, and has been in Alaska ever since.