The Sherwood Job

Sherwood: A Game of Outlaws and Arcana

Interested in [Sherwood](( Pick it up on Itch or DriveThru.

I responded to a Twitter thread about Robin Hood adventures earlier this week, but I think I’ve got a little more to say, possibly more coherently.

Sherwood is heavily inspired by classic Robin Hood ballads and outlaw romances (the latter of which often includes supernatural elements) and the fey-infused, myth-mashing 80s TV series Robin of Sherwood. I included a half-page haunted castle adventure in the ashcan, and I think Sherwood works really well with both Dolmenwood locations and scenarios and adventures created for Cairn, such as Amanda P.’s wonderful adventure Tannic.

But what if you want a classic Robin Hood robbery or prison break? Try this!

  1. Give them a person to rescue or a treasure to steal. Remember, this news rarely shows up in a vacuum: Sherwood works best when players have at least a little good intelligence on what they might be able to do, what they might get for it, and what locations they can start thinking of.

    E.g., Royal officials are holding the locksmith who helped you break into the castle’s treasure room for execution, and the sheriff isn’t even going to give them a show trial. They’re most likely being held in the castle’s dungeons (unless they’ve been sent to an interrogator), but you’ve heard they’ll be brought out to a scaffold in the castle’s lower bailey tomorrow morning.

  2. Stat up some guards and defenders. Don’t make them too generic. Add one who might be a convert (or pretend to be a convert) and become a spy. Give them another who’s got a score to settle. Give them at least one who’s going to be unexpectedly tough.

    For our imprisoned locksmith, this might include:

    • Nem, the executioner’s apprentice whose older brother was rescued a few sessions back but whose mother is being held on suspicion of knowing where his brother is.
    • Sir Creswulf, an infamous assassin who works for the crowned heads of Europe and is disguised as one of the guards (in the hopes of luring your band out to collect on a reward).
    • Elaine, an impoverished young aristocrat living in the castle who believes your outlaw band killed her lover.
  3. People who might help (or who might get in the way). Remember, most Sherwood outlaw bands have resources they can use to call in favors and may be tempted to do that if an NPC is going to get into trouble without some direction.

    For this adventure, you note that the prisoners have their meals brought to them by Jos, who despises the sheriff and is a childhood friend of the locksmith.

  4. Involve their contacts and their troubles in complicated ways.


    Every time.

  5. Give them at least some of this information. They might know some of how their contacts and troubles are involved. They might know or have a chance to learn something about the defenders. For instance, they might know that Sir Creswulf is hunting them and has come to town. They might know Nem’s available to help them, but not why he might hesitate or betray them.

  6. Add some complications they won’t know about but may have a chance to discover: the locksmith has more enemies than just the sheriff or that if there’s one more escaped convict, the king will appoint a new and more tyrannical sheriff. Give them ways to learn this and decide the complications in advance.

  7. Let them decide where and how to strike. Give them a predetermined time to talk, and don’t be afraid to comment while they’re planning. Remind them of what they know both about what they’re trying to do and how the world you’re creating together works. When the time’s up, they can keep planning, but it’s more likely that some of their plans will get noticed and require rolls to keep hidden (or that something else will go wrong: they’ve got to rescue the Locksmith, but then they saw someone who might be a sheriff’s ranger near the hideout and they might know something about the outlaws’ plans). Delaying getting started too long only gives a bad situation time to get worse.

I’ve been working a bit on a first Sherwood supplement, tentatively titled Greenwood, a book of potential opponents (and allies) with some maps and locations that can turn into heists, encounters, or adventure starters.  This is the format I'm considering for several of the starters and scenarios there.


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