How do you handle traveling in your D&D games?

There are a few things you can do, which include time-jumps, hexcrawling, and random encounters. I want to talk about the idea of travel encounters, because they serve some unique purposes, and I hate the idea of random encounters for the sake of random encounters.

There may be some people out there who run random encounters while the player characters are on the road, traveling to another destination. They do this because it’s meant to “spice up” the journey, and provide something for the players to do on the way. But…that reasoning is greatly flawed to me.

If you’re going to have a road-encounter (let’s call them “RE’s” so I don’t have to type that out every time) that’s nothing more than, “goblins ambush your caravan! Roll initiative!” then what’s the point? Why not just fast-forward to the destination if the journey was going to be so boring it needed a goblin fight?

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In talking with a friend and fellow DM, I’ve ground down the reasons for having RE’s to the following:

  • A way to add to the current story or plot
  • A way to introduce a secondary goal or plotline
  • A way to showcase your world to the players, and their characters by extension
  • A way to force your players to make a difficult choice

I’ll break these down for you.

Adding to the Story

I talked about my frustration with certain published D&D campaigns and how they seem to rely on random encounters, but I felt that they had nothing to do with the story. I then went into a bit of detail about how to “homebrew” the campaign book contents to create more impactful encounters that you control. Check that out here.

While running Curse of Strahd, I quickly threw out the random encounters tables provided in the book. What’s the point of having the characters trying to get to the next location – to the next plot point of the story – just to have a banshee or a wight come out of the woods and attack them? These are serious monsters that could absolutely ruin the day of low-level party members.

I never saw the point of throwing the party into something they couldn’t handle, and risk the characters dying, just for the sake of “spicing up” the journey. Now that character’s dead, and you have to get a new character into Barovia (if you’re letting that player still continue playing), which becomes extremely monotonous after a while – trust me.

So, instead I modified the encounters the group was going to have in order to further the story. This isn’t exclusive to Curse of Strahd. Let’s look at the following example, which I am literally pulling out of thin air as I write this.

The party is traveling from Tairseach to the capital of Halasthas, and must do so quickly – which means they cannot afford to take the long way around, avoiding the deadly Uscat desert that lies between the two cities.

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They are making this journey because they have finally discovered the true identity of an assassin that recently killed a magistrate in the trade city of Bogat, having followed their trail to Tairseach in the human-owned region of Crobayle. The reason they don’t have time to go around the desert is because an ally of theirs is pinned for the crime by the Dragul Empire, and is scheduled for public execution.

That’s your setup. The journey the party must take. Now, because the Uscat desert is such a prominent geographical feature of the continent, and because the arid landscape plays something of a role in the construction and features of Halasthas, I – the DM – will likely want to have an encounter or two as the group travels through it.

Bottom line, the desert is somewhat important. There’s lore involved. The key here is to make sure the encounters are going to be either 1) (mostly) unavoidable, or 2) worth a slight deviation from their timed task, because it’s likely that conscientious players aren’t going to want to stop for something else. Therefore, the encounters have to be related to the story.

As the group crests over a rocky rise in the dry terrain, they hear a distant scream. Looking ahead, they see a figure running from a group on horseback. They quickly close the distance and find the fleeing figure to be familiar – the star witness from Bogat who could clear their ally of the crime, the one that disappeared just when they needed him. They also notice that the witness is being chased by dragonborn of the Empire – serifs (like shire-reeves) and members of the Dragul army.

The group, thinking the witness can help them save their imprisoned ally, decide to fight the dragonborn officers.

Upon succeeding, they find that the witness was taken hostage by the serifs, and he suspects they were taking him back to Halasthas to torture or kill him. He escaped their capture while they camped, and fled into the Uscat, hoping to lose them, but they tracked him down.

The above example adds to the current story, because the witness that the party had lost in Bogat was actually captured by agents of the Empire, the same powers that are planning the execution of the party’s ally – who proclaims their innocence. So, if the ally is innocent, and the party now knows the identity of the true assassin, why would the Empire be trying to capture and silence the only witness?

Introducing a New Goal or Plotline

Traveling can be a great opportunity to tease your players with other possibilities, more stories and plots available within the world. Especially in a homebrew setting, the DM may have created several little seeds of story and plot that the players may or may not ever find. I know I have. Even in book campaigns like Storm King’s Thunder and Curse of Strahd, there are a bunch of little side-quests and little nuggets for the players to discover.

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The party is heading north on the road from Belmard, on their way to Levenstaal in the far northwest. A small caravan approaches, and stops on the road, requesting that the heroes halt as well.

The leader of the caravan sizes up the party, and nods. He asks them if they’ve had experience in hunting evil creatures, if they’d be willing to take a job. The party wants to know what they’d be hunting.

The leader says he’s coming from Shale, a small, isolated fishing village to the north. They’ve not much to offer, but are hoping that the adventurers’ good nature will persuade them to agree. Ancient legend tells of a witch that lives in the caves along the bluffs to the west of the village – a witch that transforms children into beautiful fish, and then eats them.

It’s just a tale that they tell their children to get them to behave…but, recently, several children have gone missing. The village is now gripped with fear, parents clinging to their children. Fishing and trading has all but stopped as they focus on protecting their young.

The caravan set out a two days ago in search of strong folk for hire who could come with them to Shale and help find the witch, destroy her, and rescue their children.

In this example, I’m imagining the group of heroes is merely traveling. They have no urgent goal or pressing need to get somewhere quickly. Thus, I was able to introduce a secondary plotline that they could follow for some time, unworried that they are not handling some other situation that requires their attention.

Yes, this kind of encounter or plotline could be uncovered within the village of Shale, but if I was worried that the players weren’t intent on going there, or may skip over it entirely, I could do this on the road and – like the caravan leader – play at the sympathy of the players and their characters to want to help the kidnapped children in order to get them there.

Plus, this way it’s a choice. The players, while on the road, could still turn the offer down and wish the caravan well, going on their own way. If this happens in the village, the players are much less likely to turn down the story seed, since they’re already there. So if you’re a DM that likes to offer your players many choices, here’s one way to tease some of the stories you have around them while still leaving it up to them to pick where they go next.

What if the story they were seeking in Levenstaal was more interesting to them? And they didn’t want to get sidetracked at this moment? Then your encounter might feel like rail-roading them into going somewhere else. That can happen, it’s just a matter of making it clear that it’s a choice. The caravan leader could be of hardy stock, and confident that they’ll find the help they need in Belmard, or nearby Fort Kimin, where the Vostan army is stationed. That may give the players enough excuse to feel okay saying, “no.”

Showcasing the World

This next example comes right out of my Curse of Strahd campaign.

If your players are new to the world, or your world, or whatever campaign setting you’re running for them, it’s always a good idea to give them flavors of that world through encounters. These don’t necessarily need to be combat-based encounters – but remember that, with certain players, encounters can very likely become combat-based very quickly.

This is merely a way for you to show your players what kind of campaign you’re running, it can help set the tone, it can introduce your players to the way the world works in certain cases.

In Curse of Strahd, it’s a good idea to set up the tone of the setting – the gothic horror. This was an example of when I decided to use the campaign book’s random encounter table, and threw a pack of zombies at the party as they were traveling along the road.

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At this point, they had already seen things, and done things. They had fought a vampire spawn beneath an old church. They had heard the howls of wolves in the distance, and found a mutilated body in the woods surrounded by canine tracks. They had met with the gypsy-like vistani people and had their fortunes read. They knew about Strahd.

To me, having a handful of zombies come out and attack the party was a way for me to cement in my party’s minds that this was straight-up horror. Not just vampire horror. Not just (possibly) werewolf horror. But horror. It was my way of telling them to buckle up, because they’re going to see a lot of different things.

Outside of Curse of Strahd, though, an example of setting up tone could include something like if your world contains rampant racism – if you plan on that being a recurring theme, and perhaps something that the party must face, and try to get the world to change their minds or become more accepting.

If your player party has a strange character race, like a kenku, a triton, or even a tiefling, you can use a quick little RE to show your players the type of ostracization these races may face within the setting.

A party consisting of a two elves, a human, a halfling, and a tiefling make their way down the road between a small hamlet and the region’s capital. As they round a bend in the road, they find a wagon parked off to the side, a wheel broken off. A group of six people stand around the wagon, as if waiting for something.

The party approaches, and addresses the group, who all look like they’ve been on the road for some time. A bearded man speaks for the group, saying they were headed to the capital when the axle on their wagon broke, and they have not the materials to repair it here. They sent a man of theirs to the city for help already, and are waiting for their return. His eyes linger uncomfortably on the tiefling member of the party.

When the bold tiefling speaks up, picking up on the man’s contempt, she asks if they can help in any way. The bearded man shakes his head, and addresses the human in the party, saying, “You’re either awful kind or awful weak to be lettin’ your filthy hornhead speak out of turn.”

The tiefling bristles, clenching her fists. Waves of heat emanate from them as she silently furies.

The human of the party responds, “And you’re either awful bold or awful stupid to be asking for our help and then insulting us right after.”

A couple of the members of the bearded man’s group stand, and begin to draw their knives and swords. One pulls an arrow from their quiver. The bearded man chuckles. “We’re not gonna have any trouble from the likes of you, right? Because we’re of the mind that anyone who loves the freaks deserve to go back to hell with ’em.”

I took a bit more liberty there with what could happen in such an encounter, but that’s what examples are for. I wanted to display how far I would plan on taking the racism in this setting, and how some people truly feel about it. Sorry to use tieflings as the example – they seem to get that treatment a lot – but “hornheads” was a term I already had for them, and I didn’t want to think of one for any of the other possible races at this point.

Forcing Your Players to Make a Choice

Here’s a fun reason for an RE. It should become very clear what I mean, so let’s get right into the example (plus, this post is already getting super-long).

The party is traveling with a large caravan of people emigrating across the land. They’ve come aboard for this particular leg of the journey, as the caravan leaders thought they’d need extra protection while crossing the dangerous mountains.

Along the ride, so far, the party has come to get to know a few of the caravaners, as they’ve camped and talked and shared stories. The party has opened their heart to a particular family – the Tiersovs, which consist of a wagon full of five: the father, Gerald; the mother, Yelena; and their three children. Gerald has spoken at length about his ideas for inventions he cannot wait to continue once they’ve settled in the new land.

The party has also gotten to know the handful of sellswords that are riding with the caravan, protecting them and hiring out additional help as needed – hence the party coming aboard.

As they all trek through the dangerous mountain passes, known for the primitive tribes of creatures that call these mountains their home, everyone is tense. Eyes scan around them at all times, looking for signs of danger. However, the help is spread thin along the line of travelers, as there are many of them, and few sellswords, and everyone must walk nearly single-file through the thin pass.

Suddenly, there’s an ambush up ahead, only somewhat visible. But the commotion is loud and echoes through the pass enough that it’s clear something is happening. Sellswords rush forward to defend the caravan from the barbarians coming out from behind the rocks and attacking the helpless people.

The party tells the Tiersovs to stay out of sight while they go to help the sellswords, and begin to make their way toward the front of the line, when a massive creature appears overhead, descending down into the v-shaped pass. A great roc caws a deafening cry, and extends its talons as it flaps to hover a second. Its claws close around a horse, and the Tiersovs’ wagon, and then it lifts into the air.

The party cries out after the family as they quickly ascend into the air with the giant bird, and the cries from the nearby battle bring their attention back to the barbarians, which are now clearly decorated with large feathers – aligned with the roc. The party doesn’t know what to do – to chase after their beloved Tiersovs – or help with the sellswords. One of them tells the adventurers to go and help the family, they have it handled here – even though it’s clear they are outnumbered, and people are dying.

What will they do?

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A bit of a lengthy example for the final one, but I wanted to make sure all the story points were clear on why the choice was a difficult one. That’s how an encounter can force a party of players to make a difficult choice – each will have their own consequences, and as long as you set it up correctly, they’ll be heavy consequences that the players and their characters should remember for a long while.

So, to me, those are the main reasons why you would have RE’s while traveling. If you’re rolling on a random chart, and then going, “Whelp, looks like a group of bandits ambushes you on the road!” …then what are you actually doing?

You’re stalling the characters and their players, for one. You’re keeping them from getting where they would rather be. In some cases that’s effective – creating a compelling diversion for a party trying to get somewhere fast is always fun, and forces them to make a difficult choice. But make sure there are reasons for that diversion. Don’t just throw random things at the party to stall them.

You’re also wasting their resources. This can be an effective way to make the next, upcoming challenge you have for them more difficult – in that they may be down spell slots, daily features, and healing potions – but that might feel like a cheap shot to the players, especially if it’s something random like a group of goblins or something completely unrelated to the actual plot.

If they’re racing toward the stronghold of some necromancer in order to try and stop them from completing a ritual at any moment, then have a bunch of skeletons burst out of the ground and attempt to slow the characters. THAT is in-tone with the challenge, with their goal. And it makes sense. The necromancer would do that to try and stall the heroes.

Make smart choices. Don’t waste travel encounters on nonsense. Make them count. Make them work toward YOUR goals as a DM, as a storyteller. Use them to weave intricate stories, flesh out detailed worlds, and create compelling characters – some of which might become recurring characters throughout the campaign.

What if the racist, bearded man survives, makes it to the capital city, and becomes a regular rival to the party, using both his positions within the local church and the local thieves’ guild to make the party’s lives a living hell?

What if the players end up saving the Tiersovs, and help them to settle in their new homeland? Perhaps they now have a skilled tinkerer on their side who can craft them some amazing weaponry or ammunition? Perhaps the barbaric Cult of the Roc could remain a recurring villain group too.

There are SO many options here. Don’t waste them.


Give me some examples of the most memorable travel encounters you’ve built in the comments. Tell me what encounters your players remember fondly. How have you modified existing campaign book encounters to suit your own DM needs? What encounter led to a campaign-long recurring character/group/theme?

I hope this helped you! If it did, give it a like, and share on your social media! It’s appreciated! Thank you for reading!

Until next time – Well Met!

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