Running Shadowdark for 2 Players… And a love letter to Willow
“Why does Sully always start us in fantasy’s biggest shitholes?”
I like low-fantasy, what can I say?
I have come to the conclusion that running OSR games for 2 players is not only extremely enjoyable but more laid back and easygoing for the GM than I initially assumed.
I recently ran another pickup game of Shadowdark for my brother and cousin when we made a weekend trip to a lake cabin. I ran them through Willow, Lazy Litch’s excellent micro setting. I didn’t consciously choose a setting that mirrored our surroundings but that’s serendipity for you.
Running Willow
I want to start off by saying how impressed I am with this tiny setting zine. If you are at all interested in old school DND, I implore you to check it out. At least for a one-shot. It’s so easy and approachable to run on the fly and oozes atmosphere. You can also get a lot of mileage out of it, but generally best to approach it as a starter area that players will eventually move on from.
In 4 hours of play (unusually long for me) I felt I had everything I needed to keep the game going, having done no more than just a quick skim of the zine to get myself oriented, and of course printing out pregens and a town map to handout.
We rarely had to stop to reference either the rules or the zine to figure out how a mechanic worked. When I did flip through the zine to glean information, it was fast and easy to get what I needed. The small size and neat layout of the zine made it very easy to navigate.
In short: this is my new gold standard for at-the-table usability. I will be on the lookout for more stuff like this and happy to receive any recommendations.
Where Willow absolutely excels is in its NPC descriptions and relationships. I could read about these characters for the first time and it would take less than 15 seconds to grok them. I think Lazy Litch is exceptional at providing exactly what you need to run a compelling character. It’s tight writing but it packs a lot of gameable information and fluff to help me roleplay the key NPCs.
I initially chose this zine to bring to my trip because it seemed like it would be a good fit for a smaller party of level 1 PCs. I didn’t read the whole thing fully, but I had an inkling, since it was more of a sandbox. I am glad to say that I was correct in my assessment. Willow is not a gauntlet, it’s a web. Players are given a clear problem to solve: they are stuck here. Their goal is to explore the region, the town and the network of NPCs and factions to figure out how they might be able to leave.
There is a dungeon under the town that the players will immediately get interested in upon discovering it, but entering the dungeon is itself a puzzle for the players to figure out, that encourages them to investigate the overland.
As small as it is, Willow is an incredibly dense sandbox. I don’t mean that it’s got a site on every hex but rather that each location in this setting has ties to the others. The random encounters also serve as a means of introducing players to the different factions and or showing their activities. NPCs all have their agendas which converge and conflict with each other.
This is one of the few adventures where faffing about in a tavern actually leads to something interesting. The roster of NPCs lingering in there is enough to get the players interested in something happening around the area. No matter where you go in Willow, you will encounter hooks and clues to other locations. It’s a brilliantly knotty place.
I think this sort of sandbox design, that prioritizes social engagement with NPCs and world exploration is excellent for smaller groups. Dungeons are great, but fewer numbers do put you at a severe disadvantage. Having a town and wilderness to go to and network to gain the upper hand gives players a chance to strategize and work through content that isn’t actively trying to kill them.
My brother likened the playstyle to Elden Ring. Unlike Dark Souls, Elden Ring isn’t linear, you can leave the dungeon and explore elsewhere to come back stronger. Willow’s style of sandbox offers exactly that but on a much smaller scale.
OSR games are more than just dungeon crawling, despite the emphasis on that being the core gameplay loop. I can understand why that is the case, especially with modern, stripped back systems like Shadowdark basing most of their procedures on the crawl. It’s still one mode of play in a broader game about exploration and discovery. Sure, you might spend much of your time crawling, but you don’t necessarily have to and the game can still handle the other stuff just fine.
In my last pickup game the players could only explore the dungeon. It was purely focused on the risk reward challenge of exploring room to room. While Tomb of the Dusk Queen is an excellent starter adventure, I felt an absence of a town or neighboring area to contextualize the dungeon. This is on me and not the module. I chose to keep the game in the dungeon. A one-shot doesn’t necessarily need a town, but an intro to OSR should encapsulate more than just the crawl. Having a world around the dungeon signals to players: you don’t have to die here.
Spending game time in a tavern is not wasted time if your taverns are as well designed as the Blue Brew, Willow’s only taphouse. The town of Willow is full of secrets and clues to discover that give insight into the broader region. While much of the session was spent there, I felt like the players were actively engaging with it, rather than waiting for adventure to find them.
In this game, they encountered the wizard tower before making it to Willow. As such they learned that the wizards are looking for someone to deliver them new books. So that was their initial hook that they pursued in town, meeting the book seller who informed them of his destroyed shipment up river.
After carousing they got distracted and learned more about ther Sunken Shrine. It being a foggy day, they used the low visibility as a chance to investigate and met the coral construct. I ruled that the construct speaks primordial which my brother, the wizard, could understand. Hence they learned of the items needed to appease the construct and grant them passage. Guess where those items could be found?
In the wizard’s tower.
However, after blowing their money on drinks the night before, the PCs didn’t have enough coin to trade with the Wizards. So they spent the rest of the session learning how to infiltrate the tower and steal what they needed. This led to a short heist that filled the remainder of the session.
This session was really a meandering adventure within a small area of a small map. But it still felt satisfying, because it was entirely player driven. My players, both newcomers with limited tabletop experience, had their minds opened up to the possibilities of this playstyle, and felt like they were in the driver’s seat.
So in a way, I think Willow is exactly what I was looking for in a starter adventure. It’s an intro to the playstyle that does not coddle the players, but gives them room to breathe and a weird place to get lost in for a while.
Shadowdark Compatibility
Willow is statted for Swords and Wizardy, but thankfully includes modern features like ascending AC. Converting to Shadowdark happened on the fly and was pretty easy. There was hardly any friction with the adventure design/presentation and Shadowdark’s mechanics. That said, there weren’t many combat encounters and they didn’t last more than a couple rounds at most, so this was hardly a stress test for intercompatibility.
The only moment that gave me pause was when I decided to let my players roll on the carousing table in Willow, which didn’t really jive with the fiction of the place. There aren’t guards or jails, so the players would have been exiled for their drunken buffoonery. But it was easy enough to handwave, and I like carousing results. They always have interesting outcomes.
I think running this game really showed me how over-emphasized the lethality, torch timers and always on initiative are in Shadowdark discussions. I think the “hardcore” reputation of the game is often more informed by the branding and the general vibe of its third party products than the actual mechanics. Shadowdark is no more or less lethal than B/X, OD&D, Cairn and ItO.
It’s a reputation that I worry fosters adversarial GMing and deathtrap dungeon design. We get it, your 5E party got OP and you had a bad time GMing that game. But you aren’t going to get them into Shadowdark if you act like this system is just an excuse to murder and oppress them.
Lethality in OSR games really boils down to how well the GM telegraphs danger and how the players choose to engage in light of that information. Playing smart should keep you alive. Shadowdark is no different.
Torch timers only matter when you are in the “Shadowdark”, which is basically any place of danger, and always on-initiative is useful in a dungeon or adventure sites, but not necessary in safe places like towns and taverns. These are really just pacing tools the GM can use to guide the flow of the game.
You can play Shadowdark and not use either of them. In this game my players didn’t really feel the pressure of a torch timer since they spent most of the time in overland exploration during daytime. The Wizard’s Tower was not a dungeon and so it didn’t need the crawling procedures. I still stuck with always on initiative to aid with the flow of exploration. We still had a blast.
So all in all, I think Willow and Shadowdark are a fantastic pairing. Highly recommend.
Running OSR Games for 2 Players
It’s actually fairly easy. The short answer is start your players with retainers.
Since Shadowdark was our system of choice it meant a few considerations. Shadowdark does not have hireling rules and generally de-emphasizes that aspect of OSR play, but you can start players off with a companion or two. Generate them as NPC stat-blocks, or if you are feeling generous create them as you would a PC. Just don’t turn them into a GMPC.
I started our game with the hook that the players’ guide, a halfling Ranger named Alb, had abandoned them in the forest while guiding them to the Sunken Shrine. Their immediate objective was to search for him, which led them to Willow where they found him drunk in the tavern.
This is not a GMPC. You should encourage players to have agency over this companion or otherwise use them purely to support the players in what they are doing as opposed to leading them. This makes the turn economy a bit more forgiving and gives an extra hand in a scrap. The PCs can also benefit from this character’s abilities and skills in general play. So maybe use a pregen that would round out the party for this role.
The other thing you can do in Shadowdark is grant your players Luck tokens to start the game with. I gave them each two. This is their safety net but it’s really up to them how they want to use it. Luck tokens essentially allow for the re-roll of any die in the game, but the players must use the new result. It’s not an instant win, but it is a second chance they could feasibly fail.
Those two things should be enough to buff up the party, at least so they don’t feel like they’ve been dealt a bad hand. But also not powerful enough to trivialize the content. You still want to challenge your players’ problem solving.
There are some unique perks to running for 2 players, regardless of the chosen system. Firstly, the game plays so much faster for the obvious reason that there are only two people who need to decide on a given thing. Secondly, they tend to not talk over each other as much. Thirdly, you have less scenarios where a player is left out or passively engaging with the game. Finally, it’s just easier to get 2 other people to commit to a game as opposed to 5.
My only advice would be to not structure your sessions around combat and provide plenty of opportunities to avoid a fight while not sacrificing progress. Basically, don’t run them through a railroad. If you are looking at modules, dungeons work fine but just set the expectation that combat is tougher for smaller numbers. Avoid modules that require combat challenges for characters to progress through the content. In the OSR sphere, the best modules will always provide alternatives to getting into a fight.
My experience with Willow showed me that small sandboxes are great for this type of small table. Players are incentivized to get to know the denizens of the place and negotiate deals and services to aid them. Fighting is almost always discouraged unless players are sure they have the upper hand. This leads to far more interesting gameplay where players have to think around encounters and obstacles and leverage all their knowledge and tools.
The sandbox itself becomes their toolkit.
That’s OSR at its finest if you ask me.