Are We There Yet: 3 Ways to Make Travel Exciting in Your D&D 5e Game

Today, I want to talk about a problem that I see arising in a lot of people’s games that never seemed give J.R.R. Tolkien trouble. The walk from the Shire to the Crack of Mount Doom, I think we can agree, was pretty exciting. It was fraught with danger, there were periods of tension and release, there was some marvelous scenery, and it provided room for narrative pacing. Things happened along the way.

So, why is it that when there’s a journey ahead of our players, we want to either handwave it away completely or else give the party the requisite “random encounter” to simulate the dangers of the wild? We can have a really cool starting town, full of varied and colorful characters, people that our players enjoy interacting with. We certainly have a strong dungeon or other point of interest where the bulk of the adventure doubtless lies. At least we hope so, right? But in between, we’ve just got a handful of vague descriptors at best or maybe an awkward travelogue that veers toward the boring at worst. Sometimes we just don’t even acknowledge the journey, preferring to just fast-forward to the interesting bits. I imagine we can agree that The Lord of the Rings would’ve been a much shorter book if the bits with the walking were simply removed.

Think of all the scenery we’d have missed.

How do we make the journey interesting, though? The hook was back in town and the bait is over there on the distant horizon. It’s a blank expanse between the two, right? It will certainly work if we assume the journey is not the interesting bit, that there is nothing that the road between here and there can tell us about the world, the ecology, the history, or the theme of your campaign world. The story will still hang together, but it requires a willing suspension of disbelief. Your players have to tacitly agree that while this fantasy world is rich and believable, we don’t care about traveling.

I’m not going to say that it is virtuous to enact the grueling expeditions that lead our fantasy (or sci-fi, or historical, or whatever kind of game you run) heroes from the safety of civilization to the far-flung corners of the world where adventure can best occur. I’m not even saying that getting to the good part is not necessarily the best way to handle your time in the DM’s seat. When I started playing this game, that was certainly the way we handled it. Oftentimes we wouldn’t even bother with anything so decadent as “town.” I’m simply saying that sometimes the long journeys are where we get the juicy characterization and the world-shaping grounded details that make your world really start to shine.

Don’t worry. I wouldn’t start complaining about things without coming in with a solution or two. If you’re like me, and you want to give more than a passing wave to the dangers and wonders of the road, consider the following optional mechanics and minigames for your next game.

Undertake a Perilous Journey

Our first option toward engaging players in travel and moving away from boring travelogues is not monumental or earth-shattering. If you like the way Dungeons and Dragons handles overland travel right out of the Dungeon Master’s Guide, this might be a good option toward giving the players a little more agency in how momentous or dull the travel-time passes. Really, it might be a good idea if you’re looking at your own game and, while no one has said anything to you about boring travel, you’ve got that weird feeling that we sometimes get as DMs. You know the one. It’s the one that says, “I don’t think this is quite right. Am I sure they’re having fun? What can I do to make this better?”

The inspiration for this mechanic comes from Dungeon World, which I’ve looked at in a previous article. In Dungeon World, anytime the players go on a significant journey (note the verbiage), they decide amongst themselves who will be the scout, the trailblazer, and the quartermaster. Basically, they decide amongst themselves who is going to go a little ways ahead and make sure we don’t run into trouble, who is going to choose the path, and who is going to make sure we eat and drink and rest enough to survive the journey. Everyone makes an appropriate skill check, which you’ve probably got ideas about, and assign a DC that is commensurate with the distance and relative danger of their journey. Personally, I use Perception for the Scout, Survival or an appropriate Knowledge skill (based on the type of journey) for the Trailblazer, and either an appropriate Knowledge skill, a Survival, or a Medicine check for the Quartermaster. DCs for the kinds of journeys that separate towns or cities might be as low as 10 in the case of only “mild peril,” but can quickly get as high as 18 or 20 for long distance journeys through hostile wildlands.

But what happens if you fail, I hear you asking.

Nothing catastrophic. Our fiction doesn’t benefit when failure locks away content, right? I’ve been harping on that for a while now. Instead, let the failure inform the fiction. So, if your Scout fails their roll, maybe any encounters rolled along the road begin with surprise. Your Trailblazer’s success or failure dictates how long the journey takes. If they’re hustling, there might be some drama if the Trailblazer’s roll means they miss the meeting with the High Priest or whatever you’ve got going on, right? The Quartermaster is rolling to ensure that they don’t have trouble with supplies. Does the food hold out? Do they find water along the road?


Successes, contrarily are also interesting. If your Scout succeeds, let any encounters start with advantageous position. Let them decide whether or not to engage. Their Scout saw the goblins first, do we even want to tangle with the murderous little murder-pygmies? Did your Trailblazer find a shortcut, or a secret route? Did your Quartermaster find some kind of rare fruit or veggie, some magical herb or unexpected alchemical ingredient in their ranging? These could all be hooks. They could lead to more adventures along the road!

The important part is to let your players have some stake in the journey, and then, like magic, it starts to become important to them. They care about how the dice fall. You’ve turned, “and then you get there” into something that has weight and drama. “Will you get there?” Probably. Did something happen along the way? Most assuredly. That’s where you get to show a little bit more of your world.

Campfire Interludes

Let’s go in a different direction this time. Let’s say that it’s not necessarily the journey that is lacking weight, but the fact that your players are not forging the emotional bonds of Sam and Frodo on their path to Mount Doom. Let’s face it, there’s something to be said about the feeling of camaraderie that is often lacking between new adventuring parties. You’d think that people who go pelting off into the wilderness in search of danger and treasure would probably get pretty close pretty quick. I’ve got a mechanic for that.

Now, I tend to ask about camp chores, and that’s typically a good place to start. Who gets the firewood, who does the cooking, what everyone does before bedtime, that sort of thing. What I haven’t ever gotten characters to do without prodding is talk to each other around the fire. Luckily, Savage Worlds has a mechanic for that.

Savage Worlds is another game that I’m shamelessly ripping off. See, that’s what I do. I play a lot of games, and then I take the things that I like and I think about why I like them. If I can, I drag them along with me like the very first English speaker with all of the grammar and syntax that it found in the pockets of all of the mainland Europeans, and port them back into Dungeons and Dragons. This one’s an easy, flavorful one.

The gist is simply thus: during natural downtimes–read here, around the campfire between legs of a long journey–arbitrarily pick a player and put them on the spot. Have them draw a card, because it’s their turn to tell a story. The suit dictates what kind of story they’re going to tell about their character. If you’ve been reading Drake and Dice for a while, the rhyme is going to sound familiar, and it’s still shamelessly ripped off from Dael Kingsmill. Heart for a tale of Joy, Club for Pain, Spade for Loss, and Diamond for Gain. The Savage Worlds mechanic is slightly different and there’s Love and Desire in there and generally, I like this way better. Feel free to look up the interlude supplement if you want to see how they handle it.

Did I ever tell you the one…

In general, it goes like this. They pull the card, they tell a quick story that sheds a little light on their character, and at the end they get Inspiration. It’s a quick, easy way to pull a little backstory in, mine your characters’ histories for juicy plot hooks, and also foster a little bit of companionable roleplay around the fire. There will be questions about the story, encourage people to ask. Even get the ball rolling as the DM if you have to. Take it in turns with your players. Let them all have a chance to take the storyteller role. If you’re the kind of DM who keeps track of XP in a non-milestone capacity, you might consider an XP incentive at the end of the journey. Because everyone knows that the real reward was the XP we earned along the way, right?

The Traveling Skill-Challenge

This is the big kahuna of making travel into a game unto itself. While giving everyone a job is a good first step to engaging your players, and letting them delve into their backstories is always good for fostering the roleplay that builds ties and bonds of fellowship–and Inspiration– but what if the players had to do the heavy lifting? You’re a hard-working DM, and while you are the subject matter expert on your setting, I don’t know that I’ve met a DM who didn’t like it when their players surprised them.

See, that’s a little of the juice for me as DM. I build my campaign settings in broad-strokes, because I like to leave white-space for the players to have some input on how the world works. It’s actually part of the GM best practices in Dungeon World, but, while I didn’t have a way to properly articulate my belief, I’ve been doing it in Dungeons and Dragons for better than a decade. “Draw maps, leave blanks.” Don’t get so precious about your setting that you won’t let the players surprise you with something cool. We are rapidly falling into another blog-post entirely. Back on track.

We do a lot of traveling in my campaigns.

So, remember 4th edition? Probably not, but that’s okay. It was polarizing, and if you’re old enough to remember 4th, you’ve doubtless got your own ideas about what Wizards of the Coast did right and wrong with that edition. I think the Skill Challenge was one of the things that 4th edition brought to the fore that made the game undeniably better. If you aren’t familiar, that’s okay. I will explain.

No. It’s too much. I will sum up.

Basically, we got a mechanic to create forward motion toward an objective that everyone in the party could contribute to that didn’t immediately devolve into skill dogpiling and everyone rolling the same skill, hoping for success. It worked like combat, and it had initiative, and it allowed the party’s creativity to lead to success. It was awesome. It still is.

In this mechanic, you deviate from 4th edition’s rules (not hard), and treat the travel as a skill challenge (modestly harder). Assign a number of successes that must be reached before a number of failures are accrued, then have your characters roll initiative. Take it in turns like you would combat, and ask your characters what they are doing to help the party reach their destination. This could be Survival checks to forage or scout ahead, Perception checks to discover hidden dangers, Knowledge checks to rattle off pertinent lore-bits, whatever your players can think of. That’s the part that’s awesome about this mechanic. It’s player directed.

When your Ranger forges ahead, ask them questions. Narrate the problems they face when they fail if you’d like–some people tend to describe their characters as incompetent when they roll a 1, and that’s kind of uncool–, but let them describe their successes. Ask them what they see when they come through the edge of the woodland and into the forest glade. My Ranger described a bevy of jewel-toned butterflies who alighted on a nearby tree and when they took off a moment later, the tree had gone ash-gray. The butterflies were eating the color. Ooooh. That’s good.

Teeny tiny photophagic fey.

This, doubtless, requires trust in your players and that kind of trust does not develop overnight, but when you put the journey into four, five, six, eight pairs of hands, it becomes this weird alchemical concoction in which the mundane act of trudging through the forest gets fantastic in a way that we are often afraid to let D&D get off to. Feel free to say “no, but…”if it gets too gonzo, but if everyone is on the same page, you’d be surprised how cool things get. More, you’ll be surprised how invested people become in the world when a bevy of those Colorflies go zipping by, added wholecloth to the world.


Travel is a very quiet pillar of our game. Unless you are running a hex-crawl or your characters want to play a merchant caravan or somesuch, the temptation is often just to madly teleport your characters around, relying on a network of friendly wizard NPCs to facilitate travel. This kind of smash-to-the-action storytelling is tight and punchy in ways that hearken back to the pulp-adventure stories that I grew up on, and it’ll always have a place in my heart. But if I’m going to tell a story that is broad and sweeping in scope, the kind of thing that takes us from a quiet, unassuming village and its local problems to the tremendous, world-changing machinations of existential threats? We’re going to have to travel. And if I’m going to spend time traveling, I want the getting there to be half the fun.

Thanks so much to Moebius Adventures and the Of Dice and Dragons RPG Blog Carnival for the awesome topic.

Do you have a favorite travel mechanic or do you just cut right to the action? Comment down below and let me know!

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4 Responses

  1. Erik says:

    This is great stuff, it’s going into my game immediately. Reading the traveling skill challenge section made me think of something I’ve been trying to introduce to my game with mixed success, which is the progress bar mechanic from Ironsworn.

    What I want to do is to have an abstract way to keep track of overall tension and progress. The more complications (bad rolls) the group suffers, the higher the tension should get, while progress (good rolls) should get them tangibly closer to their goal and maybe reduce tension. The trick is in the details though, because I’ve been having a hard time deciding when to actually bump each of those trackers.

    I want to use the tension level to vary the stakes based on the recent actions of the party (otherwise I tend to make everything maxed out, which gets tiresome). I want to use the progress bar to keep track of intermediate milestones, so that the game feels like a process and it’s natural to have the group earn meaningful partial victories even if they fail the last stage.

    Do you have a system you like for managing tension and progress through a story arc?

    • Drake says:

      Actually, I do! There are a couple of mechanics that I’ve shamelessly ripped off from a couple of other games. Firstly, clocks from Powered by the Apocalypse style games and Blades in the Dark are really handy for a visible representation of forward progress. Keep a circle, divided into a number of segments based upon complexity, on the table where people can see it (or not, hide it behind the DM screen and make them sweat). When they make progress, tick the clock. As the PCs make progress, let the narrative shift in their favor to represent their momentum.

      Actually come to think of it, momentum dice are a good way to handle that. Maybe they get numerical benefits based on how their clock is showing. Might be a flat bonus, or an additional die to roll. Players like rolling dice, after all.

      Clocks are also a good way to track approaching danger. Good foreshadowing tool. Maybe there’s a corresponding malus as things start going wrong…

      In general, I tend to make DM moves based on the clocks that I run, just to kind of drill in that the world is moving and to make progress (both the PCs’ and the villains’) feel more weighty and narratively satisfying.

  2. A A says:

    Hi there!
    Thank you for the great post!

    I really like the backstory card game as an idea!

    Could you give an example of this 4th edition skill check?
    I’m new to DMing and not sure how exactly this mechanic works.

    For example if i had 3 players and asked them to do a scouting/trailblazing/lore check, i place them in initiative order, and each of them perform their checks which will result either in success or failure, falling in some band of Green (everyone succeeds- really good!) to yellow (50-50, you get something) to Red (everyone failed – you botched it guys! ).

    But i don’t understand how this then works. In your example with the butterflies, it is the player who narrates? how does that work if he does not know the context (which typically only the GM knows)? Could they have said “I see the guy we’ve been looking for! He’s just there ensnared in the very trap he was preparing for us”?

    I think I don’t fully understand this mechanic. Are the outcomes of the checks inconsequential (for example like the butterflies?) or was this just an example of a ‘failure’?

    Many thanks!

    • Drake says:

      So, in 4th edition, skill challenges were a pretty unique mechanic. Unlike a simple pass/fail check, the DM laid out a situation with stakes (your boat is sinking in the middle of the ocean). Players would roll initiative like normal, and then decide what their character was doing to address the situation. Every character would use one of their skills to help, and the DM would set a DC based on how well the action suited the situation. The Fighter might use Intimidation to get the crew to fall in line (maybe a DC 10). The Ranger might use Athletics to heft some heavy repair materials (maybe a DC 12). The Wizard might try to use a Knowledge skill to determine the best way to undertake repairs in rough seas (maybe a DC 15). Basically, the DM constructed an encounter that didn’t include a monster and the players solved the problem through clever use of their skills. Depending on how nasty the skill challenge, the DM assigned a number of successes that were needed to navigate the challenge, but in 4e they had to achieve those successes before they accrued three failures. At three failures, the bad thing happened. The boat sank.

      For wilderness travel, you can do the same basic thing. The challenge is that your party has to overcome a hostile wilderness before they get hopelessly lost, or wandering predators decide they look like a tasty meal. The Fighter can lift a log and bridge a river. The Rogue can climb a tree to get a better look ahead. The Wizard can lean on their Arcana to find the old roads of the fallen empire that crossed this wilderness aeons ago…and so on. In our example in the article, the jewel tone butterflies weren’t a consequence of a failure or a success. Our Ranger was forging ahead and to add some flavor, I leaned on them and asked them to explain something that caught their attention on that day of travel. It wasn’t informed by the skill-check, just a little bit of extra flavor that made the world feel a little more fantastic. The skill challenge, as I recall, had resulted in taking a little bit more time because our trailblazer had failed the roll, but the fiction didn’t stop just because the rolls weren’t exemplary. I asked the failing player what distracted them, and I got a cool vignette about color-eating butterflies.

      These three different options aren’t necessarily all supposed to be run together. They’re each a distinct way to make travel feel a little weightier. If you assign rolls to your players as scout/trailblazer/quartermaster, then that tells you what might go wrong along their journey (quartermaster botches a roll and suddenly we have to forage for food). If you want to make use the campfire tales, that’s a way to bring some extra character flavor in what is generally thought of as downtime (you’re traveling for three days, on the second day of pelting rain, who is the one who shares a story around the campfire?) The skill challenge is the most involved, and requires the most forethought, because it expects the DM to come up with a scenario that is going to be addressed by character skill rolls (your time in the Wilderrun is more dangerous than you expected, for on the third day you feel the eyes of the guardians of the forest upon you. How do you evade them?)

      Hopefully that helps a bit! Thanks for reading!

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