HoTDQ players taking the long way

I'm unclear what the issue it. Perhaps, you can explain it more fully.

In general, use the premade adventures as inspiration and general ideas rather than hardfast rules of what should happen when. If your players are having fun and are excited about the overland travel, I see no reason to punish them for it. Just make the overland travel interesting, and roll with it with them.

Perhaps the adventure text sets up a timeframe for when things happen, but if the players don't know about it, it doesn't actually exist in the world yet unless you want it to. So, if they've heard about a time frame or deadline and willfully ignored it, perhaps they miss something. If they haven't heard about a time frame or deadline, however, it seems like you'd be making them miss out on something because of an arbitrary time period laid out in the book. You can still do this, and it can still be interesting because the players wouldn't know either way, but you have to make the call of what would help the party have more fun. If they chose the overland route simply because they want to see the world and experience more up close, let them do that and have the castle wait on them. If they chose the overland route despite knowing about the castle being ready to take off in so many days and knowing they wouldn't make it in time, then, of course, they miss it.

Bottom line, dead lines don't have to exist until the players know about them. It's cool to play in a world where things are moving on their own and independently of the players, but if the players don't know things are moving and aren't making a conscious choice that leads to them missing out on them, you're kind of just denying them experiences without them having a way to have prevented it.

/r/DMAcademy Thread