Starting
The starting point for any Underground Railroad game is slavery, and the goal is freedom. Players choose a strategy to get from the starting point to the finish line, and the game offers them several competing alternatives, each with its own advantages and drawbacks. For example, one player might forge or buy his own "free papers" that state he is a free man -- and therefore is allowed to travel without hindrance. Alternatively, another player might choose to stow away on a ship or train to get north quickly. Free papers might be expensive or otherwise difficult to obtain, and stowaways risk lack of food and air, as well as discovery.
Advances
Include several squares on the board that advance players down their routes. Such squares might be labeled "stations" or "safe houses" and confer an extra roll of the dice to represent additional stores of food and water, directions to the next safe house and new clothes. Alternative advance squares represent an unexpected cache of food, such as a cornfield, or overhearing secret directions in another slave's song, such as the one in the spiritual "Wade in the Water" -- "travel down a creek to throw dogs off your scent."
Setbacks
Some game board squares must contain setbacks. Possible setbacks on the Underground Railroad include a sudden influx of pursuers, necessitating a night or two of hiding -- or, for game purposes, a missed turn. Other setbacks are losing the way -- missing a turn or actually retreating a square or two -- or, worst, of all, being spotted by the "slave catchers," which is nearly always the end of the game.
Winning and Losing
Winning, in Underground Railroad terms, is making it past all obstacles to freedom in Canada. Losing is being caught and getting sent back to your old master, or worse, being sold even further south. Even though an Underground Railroad game couches these historic realities in the form of play, it should not try to hide the fact that for some slaves, the game was life and death: some captured escapees never got a second chance.