The game, of course, has you chasing Carmen and her gang through different places and times in U.S. history. You can visit five regions of the U.S. across nine time periods, giving you forty-five possible destinations. These nine time periods consist of the nineteenth and twentieth centuries divided into 25-year increments plus the pre-1801 era.
This game provides examples of:
- Anachronism Stew: Regardless of what time period you're in, Stretch always finds the culprit in a modern-looking apartment room.
- Droste Image: Setting the Chronoskimmer to the West in the 1976-2000 time period yields the above page image.
- Da Chief: Notably, this is the first Carmen game in which the Chief is actually seen, portrayed here as a white-haired man.
- Heroic Dog: This game marks the first appearance of Stretch the Crime Dog, who later appears in Carmen Sandiego: Junior Detective Edition and in a Where on Earth Is Carmen Sandiego? episode. Much like in Junior Detective, he helps you apprehend the crook at the end of each case.
- It's a Small World, After All: A usual for this series, but a particular outstanding example is that everything pre-1801 is lumped into one category. For example, to get you to go to the South before 1801, you might receive one clue that points towards Pocahontas and another clue that points towards the Southern theater of The American Revolution. These events are separated by some 150 years!
- Time Police: As in the earlier Where in Time, your job is to stop Carmen and her V.I.L.E. villains from stealing items throughout history.
- The Wild West: When you visit the Western states in the mid-19th century or earlier.