This post resumes my five part answer of how I prepare for an extended campaign.
Part 1: The Goal and The Antagonist
Part 2: Notable Landmarks
Part 3: Player Integration
Part 5: Ongoing Preparations
Part 4: Adventure Outline
Once you have a good idea of the game's key points and how they connect to the players, it helps to write down a general idea of how you think the story could go. Keep in mind that this is bound to change at any time based on player decisions or any events that could change circumstances, so don't get too married to the idea of your original outline. If there is a better story to be told, go with that story instead.
WARNING: MAJOR CURSE OF STRAHD SPOILERS
The adventurers begin the adventure by entering Strahd's realm and the village of Barovia. This place needs to give the PCs enough of a shock for them to understand that they're not in Kansas anymore and how different it is from their home. Everything is bleak, Strahd does what he wants, and nobody can stop him. The NPCs here will suggest the PCs go talk to Madam Eva, who gives the PCs a card reading, which is basically a plot hook for at least three different places.
When the players reach Vallaki, they should be given the hook that the Wizard of Wines has not delivered wine lately and therefore they should check it out. Vallaki is also a good way to show how twisted the realm becomes in Strahd's influence. There are many ways for the PCs to gain allies here, so they know that they're not the only ones trying to fight back.
Eventually, the PC's path will lead to the Wizard of Wines, where they learn about the druids. From there, they'll head to Yester Hill. Following my notes from the previous posts, if a PC is tied to the archdruid, they may have a difficult decision to make. If they find Strahd here or otherwise find an NPC to expose Barovia's past, this can be a good midpoint to the story where the players start to find out what makes Strahd tick, by learning about his ancestral home.
With some wine in tow, the PCs are able to enter Krezk and meet the Abbot. Even if there isn't a PC tied to the Abbot, the player will face a difficult decision on whether to play along with the twisted celestial or not. Regardless of the outcome, it'll make for good roleplaying. Krezk also serves as a way to further learn about Strahd if the players manage to bring Ireena here.
By now, the PCs may have explored enough of Barovia to feel confident enough to tackle Castle Ravenloft. Before that, however, they may want to check the Amber Temple first. In my game, the PC that was tied to Kasimir would have had an idea of how to reach the temple, and was just waiting for the best time to suggest going in. Since Kasimir's goal involves grabbing a dark power from the temple in order to use it inside Strahd's castle afterwards, he would have more reason to enter the temple first. By the end of Amber Temple, the PCs should know enough about Strahd to understand his origins and motivations.
When the PCs enter Castle Ravenloft, Strahd expects them. The PCs are there to take down Strahd once and for all, but for the Vampire, they are all his playthings for the night. As they explore the castle, they learn of Strahd's depravity, and by the time they fight, they should be made well aware of his reign of terror, enough for their victory against him to be satisfying.
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Strahd waiting for the PCs to show him a good time |
There are many other places that this adventure can go to, of course, and this is just one path that you could take your players through in order to tell the story you want. The players shouldn't feel forced to go down any given path, and they may make a detour or two, but if you place the right incentives and motivations at the right places, it'll be easier for you to lead them to the story you want to tell.