Best Times To Use Milestones In DND: Curse Of Strahd

Summary

• Use milestones like obtaining key items to level up players in Curse of Strahd.
• Completing side quests like saving Ireena or the vineyard can also trigger level-ups.
• Save leveling up for major milestones like forming alliances or completing dungeons.

One of the most popular campaigns from Dungeons & Dragons is Curse of Strahd and with good reason. The aesthetic is great; it has one of the best official villains from D&D, the area is perfect for exploring, and the campaign can be quite hard. Since the players are free to take multiple routes, leveling them up can be confusing, depending on their trajectory.

Sure, you can use experience points and just count their kills, but milestones also work well here. The book even has its recommendations for when to apply use milestones, which we’ll touch on, but it doesn’t give you enough specifics to reach level ten. So, when should you level your players up?

There will be spoilers for the campaign here.

Honorable Mention: Death House – For Levels One To Three

Curse of Strahd is a campaign that begins at level three and goes all the way to ten. That said, it’s normal for DMs to start at level one, so the book has a special side mission to start the game: the Death House.

Honestly, we have no notes here, as we highly recommend doing the Death House. It’s a great introduction, a good place to introduce Strahd if you want to, and it gets the party to the appropriate level. It can be a bit too deadly for a low-level group, but it gets the job done.

9

When Obtaining One Of The Key Items

One Level Per MacGuffin

The first thing the book recommends is to level them up when they get one of the following items: The Tome of Strahd, the Sunsword, and the Symbol of Ravenkind. With these, you get three milestones ready to go, and we also agree that it’s a good choice.

That said, we don’t recommend doing this if you put two of these items in the same place, since their location is technically random. Otherwise, you’ll end up giving them two levels right away.

If you put two milestones in the same place, such as having a milestone for completing Argynvostholt, but the Sunsword is also there, we recommend just doing one level up and using another milestone somewhere else. There are more milestone suggestions here than necessary to reach level ten, so have fun.

8

Doing The Tarokka Reading

Just In Case

If you don’t want the game to get too dangerous, a good place to level the group up is after their encounter with Madam Eva. That happens relatively early, so using this will likely be the milestone that gets the party to level four.

This isn’t a violent encounter, so using this point as a milestone is just a way to ensure your players will be a bit stronger before fully exploring the dangers of Barovia.

7

Retrieving The Bones

Saint Andral Thanks Ye

In Vallaki, there’s a whole story about the bones of St. Andral being stolen by the coffin maker, Henrik. You can level the players up once they safely return the bones to the church, thus saving the place from Strahd.

That said, retrieving the bones isn’t particularly difficult, depending on your players’ current level. If you want to make this task harder, consider having Henrik deliver the bones to Morgantha, thus tying the Old Bonegrinder into this plot.

That said, if the adventurers go to the Old Bonegrinder first, consider leveling them up once they kill the hags instead of using the bones as milestone.

6

Surviving Vallaki

Strahd Strikes

The book recommends many events in Vallaki, as it is the most developed town in Barovia. Which ones you’ll do is up to you, but we do recommend the attack on the church, which also ties in with the aforementioned bones.

Having a confrontation where Strahd appears is a good way to make things even more personal between him and the party, and leveling them up for surviving such an encounter is a nice reward.

5

Saving Ireena

Down By The Lake

Most of the story revolves around saving Ireena Kolyana, who Strahd wants as his bride. Her story can go many different ways depending on what you want to do, what the players do during the campaign, and whether they succeed at protecting her or not.

Either way, one assured way to save her for good is to take her to Sergei in Krezk. If the players succeed, then you might as well level them up. This milestone is a hard one to trigger, though, so don’t count on it happening every time you run this adventure.

4

Saving The Vineyard

Protect The Wine

This one is a bit more complicated. It’s technically a dungeon, but it’s not a particularly hard one. You should definitely reward the players here, but whether that reward will be a level-up or something else, that’s up to you.

If you choose not to level them up through the bones or the tarokka reading, this might be a good place to compensate for it because otherwise, the party might be too under-leveled for the missions ahead.

3

Killing Lysaga

Or Retrieve The Gem

Baba Lysaga and her hut are among the hardest encounters here, so you could give your players something for the effort. It also ties in with the events of the vineyard, so if you didn’t level them up there, you could start this side quest to chase the hag and kill her.

Still, leveling them up in both places is also a good way to go. The vineyard is a good place for a level five group, while Lysaga’s swamp is level eight, so they can’t go from one to the other immediately, meaning the level-up helps in both places.

2

Argynvostholt And The Amber Temple

Dungeon & Dungeon

Barovia has three big dungeons: Argynvostholt, the Amber Temple, and Castle Ravenloft. Since the Castle is mainly saved for the dinner and the end, we recommend having the characters already be level ten before going there so they can fight with everything they’ve got.

Thus, completing the house of the silver dragon and the cursed temple is worth two levels. They’re both high-level places, so using them during the second half of your campaign is good.

1

Forming An Alliance With Strahd’s Enemy

The Enemy Of My Enemy

During the tarokka reading, you’ll assign an NPC to be Strahd’s enemy. Whoever you choose, the players will still have a mission to figure out who the card is talking about, and once that’s done, they still need to convince the person to join the fight. Once this recruitment quest is done, you could level them up.

As a bonus, these are our top recommendations for Strahd’s enemy:

• Ireena: having her deal with her abuser is very cathartic story-wise. Still, since the card mentions that the ally is the evil’s bride, you could also use one of Strahd’s actual brides in case Ireena doesn’t prove a good candidate depending on how your story goes;
• Zuleika: Having a werewolf vs. vampire fight is a fun concept, and having her as the potential enemy is a good incentive for the players to go to the werewolf den. Alternatively, you can see which NPC the players like the most and turn them into a werewolf that hates Strahd to meet the card’s description.
• Victor, Kasimir, or Mordenkainen: If your party lacks a spellcaster, any of these would be good. Mordenkainen is notably stronger, though.
• Rictavio or Ezmeralda: They’re both tied well in the story, are expert vampire hunters, and can provide aid through information rather than combat.

Cards whose descriptions can be about more than one character is useful in case things don’t go as you expected and you lost the ally NPC, or if you want to swap to an NPC your players like more.