D&D 5E Escaping a Wild Hunt

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I'm putting together a challenge where the party is in the feywild in a forest realm that's claimed by the Court of Gloaming and are running to a locked portal to get them to another Court. They have angered the local Lord by rescuing the guide (who knows location & how to open the portal), who was slumbering for a thousand years for a past slight. The session ended with the horns of a (not THE) Wild Hunt echoing through the perpetual twilight of the sky.

We have a guide who's been sleeping for over a hundred years, the party unobserved but their general proximity known, and I am looking to fill about 60-90 minutes with an escape sequence., with hopefully one battle with other goals than just winning.

I do group checks for things like the whole party sneaking, and between many stealthy characters and Pass without Trace, I expect that they will be able to hide fantastically. I don't want to handwave that ability away, but I also don't want it to trivialize this. So what else can I throw at them to leverage other abilities they have.

Couple of ideas I already have
  • Need to find a particular flower (or other MacGuffin) to open the portal. Which may lead to splitting the party and changing the stealth checks.
  • Guide getting lost due to things changing in the 100+ years he's been asleep and needing navigation help.
  • Multiple valid paths, one emphisizing speed/direct route and and another stealth.
  • Detection of forcing waiting for them at a bridge and needing to either fight or detour.
(Don't want to do a running battle to get through the portal - did one of those 2 sessions back for them to get to the feywilds.)

So, what ideas do you have? How would you improve the ones I have? Especially ideas that play up on how fantastical the feywilds are compared to the mortal realm.
 

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I don't think I have any better ideas than what you already have, but I do recommend making each thing very cinematic.

For example, remember in The Fellowship of the Ring (the film) when the Hobbits are hiding at the side of the road, and the Nazgul is sniffing around for them? Once you have your PCs roll a stealth check, don't tell them if this was enough to succeed. Instead, have the creature following them get really, really close to finding them... but if they succeeded, it gets distracted and moves on.

For one thing, that's really intense (it's why similar scenes are in so much media), and two, it would be interesting if one of the PCs "breaks" and tries to attack the searcher with surprise before they're found. Just like how Frodo almost breaks and puts on the ring!
 

I'm putting together a challenge where the party is in the feywild in a forest realm that's claimed by the Court of Gloaming and are running to a locked portal to get them to another Court. They have angered the local Lord by rescuing the guide (who knows location & how to open the portal), who was slumbering for a thousand years for a past slight. The session ended with the horns of a (not THE) Wild Hunt echoing through the perpetual twilight of the sky.

We have a guide who's been sleeping for over a hundred years, the party unobserved but their general proximity known, and I am looking to fill about 60-90 minutes with an escape sequence., with hopefully one battle with other goals than just winning.

I do group checks for things like the whole party sneaking, and between many stealthy characters and Pass without Trace, I expect that they will be able to hide fantastically. I don't want to handwave that ability away, but I also don't want it to trivialize this. So what else can I throw at them to leverage other abilities they have.

Couple of ideas I already have
  • Need to find a particular flower (or other MacGuffin) to open the portal. Which may lead to splitting the party and changing the stealth checks.
  • Guide getting lost due to things changing in the 100+ years he's been asleep and needing navigation help.
  • Multiple valid paths, one emphisizing speed/direct route and and another stealth.
  • Detection of forcing waiting for them at a bridge and needing to either fight or detour.
(Don't want to do a running battle to get through the portal - did one of those 2 sessions back for them to get to the feywilds.)

So, what ideas do you have? How would you improve the ones I have? Especially ideas that play up on how fantastical the feywilds are compared to the mortal realm.
Very cool scenario! You are giving the players four objectives, as I understand it:

1. Staying hidden from the Gloaming fey riders hunting them: Based on your description of the group, I'd focus on creating opportunities to Hide via distraction, clever spellcasting, locating cover, convincing a giant beast to move (as moving cover), deactivating magically luminous "star lanterns" to create areas of shadow they can sneak through, etc. If Stealth checks come up, that's a sign something has gone wrong, and the rare Stealth checks they should be more like saving throws against discovery & should have super high-stakes attached to them. The idea being more OSR in that the players should actively want to avoid making Stealth checks, rather than putting all their faith in rolling Stealth. Flip the script, and be explicit about it. Assume that IF they have the opportunity to Hide, then they are successfully overcoming the passive Perception of the hostile forces. IF. Transfer their faith to clever thinking about how can we manipulate the environment / our pursuers in order to be able to Hide in this scene? Personally, I'd come up with a d8, d10, or d12 table of vignettes encompassing close calls with Gloaming fey riders, focusing on fey-themed stealth elements (e.g. heads sprouting from trees that scream "betrayal" when a living creature comes within 30 feet and needing to silence them to avoid detection).

2. Outpacing the Gloaming fey riders hunting them: I interpolated this from what you mentioned about route-finding between speedy route & stealthy route, implying there is some kind of a ticking clock countdown. It might be helpful to identify just what that ticking clock is. For instance, does the archfey ruling this forest realm have a costly magical ritual that requires 1 hour which seals off all routes/portals leaving the realm? Let the players know that! Are there so many riders coming to the realm, basically being recalled from other regions/planes, and appearing out of thin air, that you tell the players OOC "hey guys, in 60-90 minutes, this forest is going to be so lousy with riders that it's game over for you"? Either approach is fine, but the important thing is giving the players advance warning about the timeline they're facing – without that information, the choice between speedy route vs. stealthy route is immaterial.

3. Acquiring a flower portal key: Since you already have them navigating to find the portal, I'd consider approaching this challenge not as one of navigation, but instead as "solving a conundrum." For example, maybe there's 3 different avenues through which they can acquire the flower portal key - you might introduce one via the guide, another via a PC's backstory or past session shenanigans, and another via talking animals / monsters they encounter in the forest. (1) There could be a redcap market below the forest floor, where they could trade for one, but there are limited ingress/egress points to the market which would make a perfect ambush site for Gloaming fey riders pursuing. A further complication could come in the price the redcaps ask being a seemingly nonsensical riddle or something that puts your players in a moral quandary (e.g. maybe the flower portal key is currently in the form of a pixie with a flower blossom growing from its head, and completing the transformation will end the pixie's existence as sentient life). (2) There could be an ailing treant kept in check by evil dryads aligned with the Gloaming fey who would be able to sprout a flower portal key, if only the thick canopy choking it were cleared so it can feel the sunlight once again. However such a dramatic change to the forest canopy would be immediately noticeable by the Gloaming fey rider's ravens or blood hawks, and would attract hostile forces. (3) There could be a ruin at a chokepoint bridge over a canyon or river, which the talking animals know the buds of a flower portal key were seen in fall/winter, and likely have blossomed. However, even the Gloaming fey riders avoid it as something ancient, evil, and dangerous inhabits the ruins. Twist being that it's not just a matter of dealing with or avoiding the ancient evil (or loosing it on the Gloaming fey riders across the bridge), but also devising a means to awaken the dormant bud to blossom into a flower.

4. Navigating the forest to find the portal out: I'd aim for preparing 3 navigation choices, the first one between A or B, the next between C or D, and the last between E or F. Each set of choices has a stealthy option (which should also include some hidden threat in the shadows that I'd foreshadow with my description of what that path looks like) & an expedient option (which should include some kind of obviously foreboding terrain hinting at the skill checks which would be involved, as well as few to no opportunities to hide). When they take a stealthy path, there should be a risk of burning time off their clock when they fail checks or make certain decisions. When they take an expeditious path, there should be a risk of giving away their position to hostile forces.

One last thing: I think, if I've interpreted your scenario right, you've got enough here for 60-90 minutes gaming, no problem. Maybe more than that. No need to throw in a fight at a bridge or at the portal out, unless you really wanted.
 

As a PC, I would want to leave booby traps and surprises littering my path, for the pursuing hunters to stumble into. What plants / wildlife can I use to mess up the hunters and/or their hounds?
An assassin vine,
Plant Growth something covered with thorns so it blocks the path,
a snare tied to a sapling,
pit traps with spikes,
"No Trespassing" sign; forge somebody (very powerful) else's signature,
long-range longbow shots across a meadow,
stampede wildebeests into the hunt's path - either to run them over or at least ruin tracking my trail.

All this can cost the Hunt time and resources, even if it does not break down or give up.
 

Of course there's the fun that you get if they accidentally stumble into a hostile creature that could delay them and cause a lot of racket in a fight.
 

I do group checks for things like the whole party sneaking, and between many stealthy characters and Pass without Trace, I expect that they will be able to hide fantastically. I don't want to handwave that ability away, but I also don't want it to trivialize this. So what else can I throw at them to leverage other abilities they have..
I'd throw one potential challenge to potentially thwart this amazing stealth, but it really depends on the morals of the party. While the party is hiding, have them come across an innocent looking creature, perhaps a fey child. The creature must call out to the Wild Hunt, or else face their wrath. The party will have to silence the creature to avoid detection, but how far are they willing to go to do it? The details depends on the group and yours style, possibly allowing for negotiations, bribery, intimidation, kidnapping, assault, and possibly even murder. You might even consider possible outcomes and future complications that arise from it.
 

You can have some spells act more powerful in the few realm. Plant growth could affect 2x the normal amount.

You can also have a good encounter where mounts offer to aid the PCs. Maybe not flying, but intelligent enough to have something they need and offer trade.
 

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