Riding through England is the most complex entry in The Riding series, with several extra rules intended to simulate the railway history of England and Wales. Players buy shares in 10 English railway companies, build routes between cities, buy up old historical lines, and receive income. The most notable change to the game system present here is the end game, where the previously placed lines are privatized via a closed fist auction.

The game focuses on the transition from the private railroad companies to their consolidation as a consortium (similar to Länderbahnen), a process that makes for a challenging game, primarily suitable for advanced economic gamers.