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in an upcoming session it is possible I might have to handle a chase between cities.

I'm DMing Tyranny of Dragons and we are going a bit off book (not a problem, in fact I like where the players are taking this) and the party might be in a situation where they're going to have to track one of the villains from Baldur's Gate up to Waterdeep (instead of getting hired as caravan guards as the adventure suggests). Depending on how things play out, the villain may have up to half a day head start on the party. The chase will likely happen on horseback.

I've been reading up on skill check type of chases, but they all seem better suited to more immediate chases (villain escapes out the window, party gives chase through the city).

Any ideas on how to handle chases over large distances?

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    \$\begingroup\$ For answerers, keep in mind our subjective answer expectations; we aren’t looking for untested ideas, we want tested, experience based answers. \$\endgroup\$ – Thomas Markov Apr 29 at 21:13
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    \$\begingroup\$ Answers so far are about making chases dramatic, but are you looking for RAW how to handle skill check chases involving long distance travel? \$\endgroup\$ – Kirt Apr 30 at 6:31
  • \$\begingroup\$ There's such a long-haul chase happening in Out of the Abyss. If you have that story available, check how it's done. \$\endgroup\$ – Olivier Grégoire Apr 30 at 13:11
  • \$\begingroup\$ One important detail: does the villain know they are chased, or is the villain paranoid enough to think they could be chased? That is, does the chase start the moment the party is close enough, or did it start since the villain left town, the party is playing catch-up, and there's going to be obstacles in their way? \$\endgroup\$ – Matthieu M. Apr 30 at 17:51
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My suggestion maybe seems a bit railroady...

...but your players won't necessarily know.

I DMed some chases (it was my home-brew system, but that issue is interchangeable)... and every time I started by writing an end for this situation or at least had some scenes in mind where it could be possible to catch the target.

The first chases I DMed were roll/skill-based... and that's just super tedious... it feels like Mensch ärgere dich nicht... I can't recommend to do that. It's just random and your players won't get the feeling that they can do much about it.

Rather give your players something to do and decide if they catch their target depending on how well they did that "something".

Here's an example

(Alert! That will be a longer story, but I try to keep it short):

The party was more or less stranded in a jungle after they escaped from prison. They got in jail because of their former client. That client was also responsible for the loss of their airship and they were pretty much pissed about their soon to be frenemy. They were pretty much low on supply and lived with and from the jungle for a few weeks now. They had some encounters with local cults and even a demigod called Samedi (yapp, like that Voodoo-Guy), wich was the big bad of that part of the campaign... when they heard a steamboat (it was a steampunk home-brew world) crossing the stream where they camped. On board were some men in sailor uniforms aaaaaand their former client. They had a little argument about money he owned to them... let alone the costs of their ship... and the reward for their last quest... and their arrest... etc. It was a pretty heated discussion and I almost thought, that this guy is pretty much dead. But I counted on my greedy players... and it worked out. He had this sailor guys hired for his dangerous expedition to recover a very valuable McGuffin and his boss will pay good money for that... they won't get only the reward from their former quest and a part of the reward for this quest... no, his boss will get them a new shiny airship. They were stranded anyways... so they pretty much fell for it. And it came how it had to come: The client screwed them again and left them in a trap room while he stole himself away (with the McGuffin of course). When they finally made it out, that jerk was far ahead. He stole the steamboat and abandoned his crew... again. One of the party's casters recently learned a spell that allowed exceptional fast travel, but through the shadows... it was pretty much my equivalent of the Border Ethereal, but more like Warhammer 40k's warp space. And this part of the shadows was controlled by that demigod the party ran into before... so they were trapped in his labyrinth, had a few quests to do to prepare for a huge boss fight, killed the demigod, left the shadows just in time (they did it exceptionally fast), catched their former completely surprised client and tied him up. They didn't kill him yet... because they still wanted their money... so he had the opportunity to screw them a third and last time. He ended up in a volcano shortly afterwards... but that's a story for another day.

Before that campaign I had a investigation/puzzle chase... pretty much the whole campaign was a huge chase after an OP-Mary-Sue(ish) shape-changer assassin pumped up with magic items and combat drugs.

It all began with some murders that led the party onto her trail. After a few encounters with this crazily overpowered enemy, they found out that she was looking for some kind of weapon or device that is able to focus the power of dead gods and do... stuff with it... I don't want to explain to much... so this should be enough for you to know at this point. I didn't know yet how they would end up in the show-down scene, but I already knew where that battle would be: On the deck of the McGuffin that happened to be an earth-dragon-ship that was able to phase through solid material. Dragon ships were also a thing in my world... Dragons were extinct elementals and their bones were used to build ships that inherented parts of their elemental power. Because of their phasing abilities it was exceptionally difficult to get some earth dragon bones... so that ship was kinda special or to be more honest the only one of its kind and it was deeply hidden under the city that campaign played in. But I digress... It was pretty much a scavenger hunt, stuffed with puzzles and hindrances, one dynamite infused prison break, a journey almost halfway around the world, some almost lethal encounters with Mary Sue (I didn't know it better back then) and a hidden invasion clock ticking behind my DM screen. Because everything Mary Sue was doing was preparation for their bosses to invade the party's home city. When they finally found the McGuffin and started its engines to meet up with McGuffin person (that was an elemental being entitled to restore balance to the world by using the ship's energy... blablabla... again: I was a much worse DM back then^^). They had their fight, now leveled enough to prevail while the battle for the city was raging.

Long story short: Think those situations backwards. From a possible key scene in reverse to your party's actions. At least that worked out in the past for me.

And a third rather short example that's pretty much how you should NOT do it... because it's TEDIOUS!

I had that Cthulhu Campaign in which my party was a mafia gang. They had that heist, where they got screwed by their partners (yapp, I like that trope) and chased after them. The following car chase were opposing driver checks. So I rolled, they rolled, they got closer, their opponents got further away, they tried to shoot the tires... it was just forgettable and didn't create any memorable situations. Because I didn't plan anything and trusted the randomness.

The problem with the last example: You give away control where you don't need to do that and that leads very often into very awkward situations where you wanted to create a Hollywood blockbuster action scene. It can get very funny if you trust your and your party's story to random factors.

Another big but more general tip: Don't let randomness decide whether your party prevails in their story or not. Let it rather depend on how fast/creative/efficient your party solves the hindrances you throw at them... at least, when it comes to off-combat situations. Let it be a battle for creativity rather than for pure randomness.

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I recommend making the chase less like the one in LoTR The Two Towers and more like a sort of scavenger hunt. One hint leads to another.

The party tries to retrace the steps of the villain, but are not actively chasing right behind them. Otherwise, the players will try their hardest to catch up, which might not be as viable or fun as investigating where the villain has been and where they went next. Specially if it's your intention is for the party to end up in Waterdeep, and not catch up to their prey beforehand.

This also gives you as a DM much more flexibility. Give the players plenty and varied ways to find the trail, and the fun is in not losing it, instead of frustratingly being too slow.

To summarize, parties are usually like puppies, don't try to make them chase something they can't catch, or they won't have fun.

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    \$\begingroup\$ Welcome to RPGSE! While your answer seems very plausible and to be a very good tip, can you support it with some examples from your experience playing/DMing such a chase? \$\endgroup\$ – TheKhileyan Apr 30 at 8:58
  • \$\begingroup\$ Sure. I have both DM'd and played a handful of chases now. Specially since it's becoming popular that some enemies don't fight to the death.The general feeling I have sensed is that chases are extremely stressful if the players end up feeling they can't catch up to their enemy. I would highly suggest avoiding chases if the aim is for the players to follow a trail instead of actually catching someone \$\endgroup\$ – Yael Araizaga Apr 30 at 14:47
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    \$\begingroup\$ I meant: Can you add some examples to your answer? Answers without the support of quotations or first-hand experience examples tend to get downvoted on this site. See it like a self-moderated encyclopedia. Opinion-based questions and answers get deleted very quickly. \$\endgroup\$ – TheKhileyan Apr 30 at 15:17
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You can introduce setbacks, or give players "short cuts," enabling them to effectively catch the villain.

If the villain is a considerable distance away, and they have any indication of where he has been, they could cut him off from ahead if another road led to his location. Alternatively, the villain may have had a number of horses die in a rock slide, setting his men back by a day.

Bread-crumb style storytelling is also quite effective. Have the players search for locals to see if anyone has seen him, then set off on horseback tracking him down. Possibly searching for tracks, the remnants of a camp, or any other travelers on the road that may have seen him.

As long as you're not having them make opposed checks to see who's faster, they'll have a good time. You control when they catch up to him, and you decide if the amount of effort they've put in means they have caught up to him. Just make the journey there as fun as possible, and you'll do great.

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    \$\begingroup\$ While your answer seems very plausible and to be a very good tip, can you support it with some examples from your experience playing/DMing such a chase? \$\endgroup\$ – TheKhileyan Apr 30 at 8:59
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For an officially published approach: Out of the Abyss (roughly chapter 2), has a longer chase section, not with towns, but that could be adapted in as it is weeks or possibly months long.

Basically: the DM tracks a score of how close the chasers are, and rolls daily on random events, which can raise or lower the score (also dependent on how the players interact,e.g.: do they cut the rope bridge behind them?). Skipping long rests gives a couple of points +, taking short rests a bit -. Encounters take time: -. Below a certain score they will have to fight scout parties of the chasers (and if they let them flee big minus points), at 0 they're apprehended. At a high enough score they loose their chasers (who will then use their contacts everywhere to keep a lookout to restart the chase.

It kinda works but only if you enjoy random encounters imho. I wouldn't favor it, but if you have access to the module, you know where an official ruleset is. Cities should be just another encounter giving + or - chase points depending on how they act.

[Edit because I read that as your party being chased, however, the base idea imho still applies, just that your party is presented with the attempts at scorched earth or traps that the villain left behind, catching up after doing the fast thing often enough or loosing ground (and therefore older tracks / less "having seen"s from passer bys)]

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