Sheriff of Nottingham: Merry Men contains five modules that can be added to the base game, as well as the option of including a sixth player. The five modules are:

- Deputies: In six player games, you may use two Deputies instead of a single Sheriff. Here, both deputies must decide to search bags or let people pass, and they will share the punishments and rewards. If a deputy disagrees with the other and searches a bag, they will receive the punishment or reward by themselves.
- Merry Men: Adds new illegal goods in the form of 'merry men' characters. If they are successfully smuggled in, players will reveal it and activate its special ability.
- Black Market: Adds three sets of bonus cards that display illegal goods. The first player who successfully smuggles in the indicated goods receives the bonus cards and a large reward.
- Laws: Sheriffs must draw three law cards and choose two to keep. The chosen laws are in play for the entire round.
- Special Orders: Special order cards indicate combinations of one legal and one illegal good. If players can smuggle both of those items in the same bag, they get that card, which provides them with bonus gold.