)Not a simulator by any definition, but looks promising.
About: Transport Fever is a railroad-focused tycoon game. Players start in 1850 and build up a thriving transport company. As an emerging transport tycoon, the player constructs stations, airports, harbors and makes money by connecting areas requiring transport services.
Construct complex road-rail-water-air networks in the endless game and experience more than 150 year of transportation history.
https://www.gog.com/game/transport_fever
