Trans-Siberian Railroad — originally one of three titles in Winsome Games' 2015 Essen Set — shares some similarities with older Winsome titles in which the rail network is already printed on the board and individual railroad companies purchase the links that are printed. Four companies (Red, Blue, Green, and Yellow) are active at the start of the game, with one share of each company auctioned to the players in that order to provide starting capital for those companies. The winner of each auction chooses an unoccupied link from Moscow to another city; each link has a value listed in it, and the railroad's initial income is set to this value.
