City Connection has one or two players (taking turns) driving through a total of five different cities. The five levels resemble New York (USA), Paris (France), Neuschwanstein (Germany), Egyptian temples and a lakeside area.
As each stage is traversed, the road behind the car turns white as it is painted, to show where the player has driven. Several obstacles attempt to stop the player's car such as police cars, cats and spike strips. Once all blocks in a level have been painted, the player moves on to the next stage. Random red balloons will appear, if the player grabs three in the same level, it will warp them ahead a few levels and provide bonus points. Even if the player ends up back in New York, the difficulty will stay the same as the previous level warped from.
Each level has its own musical track, although they all resemble "Allegro non troppo e molto maestoso" from Tchaikovsky's Piano Concerto No.1.
City Connection's general gameplay is similar to Miner 2049er which was released on several platforms including the Apple II, Atari 2600 and 5200, Commodore 64 and ColecoVision. In that game the player must fully investigate mines.