I started running a game with my neighborhood gang for Horror on the Hill, a classic module from the 1980's. Meanwhile, my high school group voted to do Curse of Strahd. The high school gang was formerly "The Pillories", the party that played Lamentations of the Flame Princess over the past year and recently wrapped their campaign. Originally we were going to do a Call of Cthulhu next, but I wanted to get some more "drive time" with the Shadowdark rules set, and we talked about several different campaign ideas. They ultimately picked Curse of Strahd. Curse of Strahd (COS) was originally written for 5E, but don't hold that against it, and it seems like it will work fine using Shadowdark rules. We're 3-4 sessions into the campaign, but this post is about the conversion process and getting the campaign set up.
There are a few good 5E campaigns that lend themselves to a retro style of play and sandbox gaming - Dungeon of the Mad Mage, Tomb of Annihilation, and Rime of the Frostmaiden, for instance. Curse of Strahd occupies a nearby place - it’s a little verbose and almost wants to be a plotted or scripted scene-based campaign, but it's also set up as a hex crawl in the valley of Barovia, with Castle Ravenloft and several dungeon sites. There's a small cottage industry in the 5E crowd of converting Curse of Strahd into a full-blown scene-by-scene adventure path, but it seems easy enough to go in the other direction too, and bring to the foreground the sandbox elements and player agency.
As written, the campaign suggests gifting experience levels to the players as the players wander Barovia and do stuff - it's more exploration focused than the scene-based milestones that show up in adventure paths, but doesn't go all the way towards an "XP for Treasure" mode like I'd want in a retro sandbox. The first thing I wanted to figure out was how much experience the campaign gives out naturally if you tried to run it as an XP for Treasure campaign. It was a little tedious, but I tallied the treasure finds from the hex-crawl locations and dungeons. I also assumed characters will get to go carousing several times, as XP for carousing seems to be a default assumption of Shadowdark, and fits one of the themes in Curse of Strahd - Barovia is dreary, and wines and spirits are one of the few things that bring joy to the dismal landscape. The total XP in COS a little light - there's enough XP for a party to get to level 6 if they "collected most of it" which we don't necessarily want to encourage. So the XP will need a little juicing - either adding treasure to locations where it's sparse or nonexistent, increasing the reward amounts, and/or adding some boon or quest rewards for major accomplishments. Shadowdark doesn't use a 1gp = 1xp basis; the game uses an abstract system where treasure hordes are worth either 1xp or 3xp, and legendary items are worth 10xp. I've seen where referees use a 5xp category for major hordes and I think that change could be effective at increasing the campaign's overall XP. One thing I'll mention - the actual gold piece counts found in a 5E adventure are right in line with Shadowdark's recommendations - which is somewhere around 1/10th the amount of treasure you'd see in an old school game.
Sly Flourish has been running Ravenloft as a Halloween one-shot the past couple years and uses 5th level PC's for Ravenloft (the original I6 was for characters levels 4-6) so I imagine 5th-7th level characters would be fine for the finale of COS. It won't take much adjustment to the campaign's XP to ensure player characters can get into that range before they head to Castle Ravenloft for the final confrontation with Strahd and the brides.
If you're familiar with Curse of Strahd, you'll know there are several meaningful accomplishments the characters can do along the way that could represent XP moments: lighting the holy beacon of Argynvostholt, discovering Strahd's secret at the Amber Temple, finding the lost Arabelle (Madame Eva's heir), restoring the Wizard of Wines Winery, and so on. Shutting down Old Bonegrinder or rescuing children from the werewolf fighting pits in the western caves could fit as well.
Regarding monsters: there are online guides on converting 5E monsters to Shadowdark, so that wasn't hard to do. I think I ended up with about 40 converted monsters in the monster document I made.
The last piece to prepare for sandbox play was to have clear notes on plot hooks and connections between non-player characters, locations, and what the players can learn. There are 14-15 places to explore in the valley, and varying amounts of NPCs to meet in each location. In an adventure path, the author will dictate patrons or events that push the players from scene to scene; for the sandbox, the players have the agency, they're the ones doing the pushing, and the referee's job shifts to making sure they have the opportunity to get enough information to make meaningful plans. The hardcover of Curse of Strahd is text-heavy and verbose; I found it helpful to make an outline for each location of which nuggets of information can picked up at each locale or NPC. There's a natural flow to the campaign, with the opportunity to engage in side quests and detours depending on player preference.
And voila - that's how I've turned Curse of Strahd into a retro style sandbox. I'd be glad to post the quest outlines or monster conversions if there's interest. Otherwise I'll get some game reports rolling on how we've done so far.