EDIT: This blog entry is a living document. As I learn and read other people's solutions, I update this page periodically. Although I may occasionally copy someone else's original text at the top as notes during that process, I am not claiming authorship of their work, and will delete it once I have parsed their ideas to work within the context of everything else I know about this topic. When people ask for this kind of help, I link to this page as my answer. /EDIT
OK, so like, I know 14 is kind of a weird number, but that's how many I got, so deal with it. A lot of players struggle with overland travel in RPGs. It seems like there's nothing to see or do, and travel just turns into a series of ambushes between important locations. Look, I know overland travel seems impossible to do right. Somehow, there's a fundamental ludonarrative dissonance between what we know an adventure is, and what the game winds up generating. It only took me around 14 years to figure out what the problem was. Fair warning for the TL;DR: like everything the DM is in charge of, it's your own fault for being uncreative and lazy. I've been noticing a trend with all of these things I used to be bad at that everyone else is also bad at...
(As an aside, if you want to explore the dissonance thing, you should check out gameplay and story segregation. Knowing this is a thing is the best way to stop yourself from doing it wrong.)
Before we go trying to make adventure fun again, I'm going to explicitly agree with Angry about something. If your idea of adventure has nothing to do with exploring the world, then you do not need to do this. Skip it. Hand wave it. Gloss over it. If your idea of adventure centers on actions or people, and you think of journeys as the mundane logistics of simply getting from place to place, just don't bother with it. Do a cutscene telling the players about their arduous journey, or just fade to black and say it happened off-screen, and move on to the part you actually care about. No amount of record keeping or creative encounter generation will make something you don't care about interesting. If you aren't having fun, your players most likely aren't either. You need to be in it for real for it to work. There. Now, everyone who wants a classic adventure, the kind where you venture into the unknown world, read on.
The root of the problem has two branches:
Firstly. An unread DM is a starving DM. Read novels where characters go on long journeys by foot. Read how the author handles the experience. Read a lot of books like this. Absorb all of their techniques. Watch road trip movies- especially comedies. Watch survival movies. Watch nature shows and documentaries. Research historical methods of travel and Exploration. Beyond the literature though, practical research makes all the difference. Go for a hike. Go camping. Walk in the woods. Walk in the rain. Walk in the snow. Learn to ride a horse. Learn to row a boat.
Far too often, we cocoon ourselves in modern comfort for years on end, experiencing nature in only the most distant and impersonal of ways. Go out there. Feel the earth under foot. Taste the humidity of a forest. Scrape your knees. Sleep under the stars. Experience this earth for what it truly is, in all its beauty and glory, for all its discomfort and danger. Appreciate the millennia of human labor which have provided us a world that is comfortable, reliable, and safe. Respect this vast and powerful world which, to this day, can simply choose to kill us in an instant if we do not prepare accordingly.
Secondly. A modern DM is a spoiled DM. Today, a 2 hour drive from one town to the next is a boring interruption to our day. We look out the window and see all the same; trees, hills, farm houses, stock animals, fences, and the ditch beside the road. It can be hard for a modern person to remember that just because this is the way the world has always been for your entire life, this is not the way the world has always been. In ages past, where now we see mild pastures and overpasses, there was naught but wild lands, untamed and unexplored, mysterious, perilous, and awesome. That two hour drive could take a whole day, even if there was a road. If there was a road, it was likely little more than wagon tracks in the mud. Travel was decided by weather, and meteorology involved talking to angels by throwing sheep knuckles in a bowl- and even that didn't work very well because God was ineffable anyways. Maps were expensive, hand-made practical art objects which took years to craft, and often got the details wrong. The world was a much more complicated place to travel back then- a place ripe for true adventure to happen.
For travel to be an adventure, it needs to involve exploration. There need to be good reasons to take the road less beaten, or to check out that odd landmark in the distance. Spending extra time in the wilderness is a risk, so it should be rewarded. Every time the players are going to cut a straight line across the world map, there need to be a myriad of twists, turns, threats, distractions, and surprises to take them off that path. The only things that really travel in straight lines are airplanes.
Without further adieu, here are the tips on how to bring that adventure to fruition.
1. Track time.
Describe how the aesthetics change as the day goes by. Both light and weather vary as the day goes on. It may start beautiful but end in a terrible storm, or be gloomy all day, or seem beautiful but turn out to be miserably hot, etc. It matters whether it is night or day, and how long the shadows get. The time of day should alter the types of wildlife you're likely to encounter. It should impact the weather. Light controls visibility, not only during combat, but also for exploration.
I generally run an immersive experience by the hour. If you travel by the day, the abstraction becomes too extreme, and forces you to abbreviate descriptions. When you describe everything that happens in a day, it stalls play by taking away any opportunity for the players to roleplay in that day. It steals player autonomy by never even giving them an option in the first place. Daily travel works better for a hex crawl, because it heats up the adventure's pace and reduces the number of encounters, (which are usually mostly combat in a crawl) making it more reasonable for the heroes to survive travel.
In 5th edition, you can use daily travel to award downtime days that players can spend on downtime activities during their travels. If you do this, limit the downtime activities to the kinds of things they can do away from civilization.
Pro-tip: When you want to emphasize the boring emptiness of a region, the dragging of time, there is a way to do it without being boring: When they state that they are doing nothing as they travel, stare at them in absolute silence, don't even respond to them, for exactly 45 seconds before continuing with the next hour or day of exploration. The silence and awkwardness will make their skin crawl. Don't use this too much, or it'll be truly boring, but it can be quite jarring if used to point out that their last decision is stalling play.
We'll come back to this, but routines are a powerful tool for marking and measuring the passage of time. The party wakes up, eats and drinks, camp teardown, they study and update maps and journals, prayers and spell preparation... As they travel, animals stop for rest and feed, distractions happen, lunch... As the light fades from the sky, they search for a good site, set up a camp, eat, rest, plan watches... and it all starts again the next morning. The farther they travel, the more days pass, and the more resources they burn through. Day after day. The moon goes through its cycles. The constellations creep across the sky. Weather drags or changes. (If it rains for a week, that's memorable- but so is that surprise hail storm in the middle of a month-long heatwave!) Holidays come and go. Seasons can pass. All various cycles, slowly measuring the passage of time.
Time is a resource, above all else. Remember, time is what consumes their other resources more than anything else. In effect, their supplies are just a really abstract method of buying time in the wilderness. As they travel, they slowly run out of survival time. If they stay in the wild for too long, especially in inhospitable places, the world will quickly begin to kill them. The real danger of running out of time gives a sense of urgency to play, and makes characters like rangers invaluable to long-term survival.
More than that though, the world should never stop turning, and should not revolve around the heroes alone. Things should keep happening in the world as the heroes travel and do things themselves. Unlike a Bethesda game, where the villain happily waits around for you to finish every side quest in the universe, a D&D villain should be actively working towards their goals. Wars should play out in the background. The consequences of past quests should manifest over time. Natural disasters happen in far-off places they've never been to. The local scandals and gossip shifts. The landscape changes in the decades since their map was drawn. Even the heroes' current goal should be a sort of moving target!
Did Lizardfolk kidnap a bunch of villagers to eat them? They have a limited time to save those people before the lizard men get the fires ready and start cooking! But do they take the easy/slow route to save combat resources, or do they try to hack their way through the dangerous/fast route? Or do the players have some other trick up their sleeve? And should they even bother with this when they know the real threat is the dragon the lizardfolk worship, and they only have so much time before it successfully marries the king's daughter?
Time introduces tension, and when you give the players conflicting goals which compete for limited time, it forces those players to make decisions and get creative. It forces them to play.
2. Track weather.
Tell them if it's getting warmer or colder out. Tell them if there's a breeze. Mention environmental effects, like storms on the horizon, or seasonal effects like trees in blossom or losing their leaves. Mention any wildlife they see. (Someone might go hunting, or a player may be looking for an animal companion. If nothing else, it's texture.) Weather is the single biggest issue in ancient forms of travel. It affects everything. It decides when to travel and where to travel. It changes which route is fastest. It changes resource availability. It affects the difficulty of navigation and the speed of travel. It can kill you. It can save your life. In the wilderness, mother nature is empress, and the weather is her word.
Remember to include weather effects when encounters happen, too. Maybe a dragon flies overhead, but it's so overcast all they hear is the slow, melodramatic beating of its leathery wings through the clouds. Maybe they're beset by wolves, but howling wind interferes with their ability to hear each other, making it difficult to coordinate tactics. Maybe the rain has turned he road to mud and the whole battlefield is difficult terrain! Your weather effects are the first and easiest properties you can apply to any encounter to change the context, tactics, or difficulty.
Weather can also introduce new types of encounters. A road might turn into a shallow stream during a torrential downpour. A blizzard might force the players to seek shelter in a ruin. A drought might cause a river to dry up, becoming a treacherous ravine.
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| Angry has named this solution to random encounters the "genauein" solution. It's a contraction of German "genau ein" which means "exactly one". |
3. Different types of encounters.
Before I talk about the various types of encounters I run, I should give a word to the way a travel encounter should be played out. Remember, the players aren't playing if they aren't making decisions. While making tactical combat decisions does benefit the players, those decisions don't mean much. At the end of the day, combat only has 2 results: win or lose, and all of their decisions lead to one or the other. In other words, combat offers plenty of options, but few actual choices:
breadth of an ocean, depth of a puddle. Because travel isn't an option, (they MUST get to B from A) the players aren't actually playing a game during that process,
they're waiting. Every encounter is an opportunity to get them playing again by giving them choices to make. The more engaging the choices are, the more engaged the players will be. For choices to be engaging, they need to make a difference and be relevant to the task at hand. Since the task is getting from A to B, their options need to affect travel resources, including time. Encounters which offer options to change course or go off route are also a good way to get players discussing what to do, getting them to focus on PLAYING the game again.
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| This is a vignette. |
Also, the encounters need to have narrative value. They need to have a purpose, even if they are random. Don't just state the bare-bones minimum of what they stumble upon. Describe the who, what, where, when, why, and how of it! Give it details! Paint a picture in the mind of your audience, and paint them into that scene. You often hear people describe encounters as "vignettes", which are small scene paintings. That is exactly the advice I would give to you. Every encounter is a chance to deliver a plot hook. Every encounter is a chance to show the players some lore of the world. Every encounter is a chance to distract the players. We are here to immerse ourselves in the emergent product of our combined imaginations.
For each hour of travel, I first roll on a chart which tells me the
type of encounter they run into. (Not whether there is an encounter at all) Combat encounters are generally rare, but some areas are weighted differently. Now, most people assume "encounter" means combat. That is not necessarily the case. Really, any time the players enter a scene, that scene is an encounter with the setting and system. That's where the word comes from! Some like to divide encounters into 3 types: exploration/interaction, roleplaying/socialization, and combat. I generally follow that model, but I find that the exact demands of travel requires rather specialized versions of those categories.
First: There are environmental encounters;
such as...
- obstacles in the path, (gorges, rivers, ruined roads, fallen trees, etc.)
- hazardous terrain, (quicksand, tangling vines, falling rocks, sinkholes, rickety bridges, etc.)
- hazardous weather and natural disasters, (storms, tornadoes, minor earthquakes, blinding fog, avalanches, floods, forest/brush fires, etc.)
- civilization encounters, (an inn on the road, a farmer's home, a hunter's lodge, an old shrine, an abandoned hut, a logging camp, etc.)
- and pretty things, (gorgeous rock formations, pleasant Meadows, foreboding woods, ancient ruins, huge flocks of birds, etc.)
Second: Then there are NPC encounters; wandering merchants, toll roads, con artists and criminals, highway patrol guards, hunters, wandering minstrels, other adventurers, funerary processions, nomads, pilgrims, mysterious strangers, farmers, road workers, beggars, people in distress, lost wanderers, guides, caravans, taxis, missionaries and evangelists, weirdos, etc.
A lot of times we have a habit of glossing over these people (or even pretending they don't exist) but it can be worthwhile to make all strangers potentially worth meeting. Give them a little backstory, some sort of goal, a secret. Let your party decide how they interact with the character, but give them enough juice that they have a choice of involvement. To make it worthwhile, simply record every NPC they encounter and how the encounter went. Then, keep every single NPC in a big toolbox. These characters are your tools to deliver new experiences in the game. Whenever one of your old NPCs could be useful, whip that character out and have the relationship pick up from where it left off! These little, "hey, aren't you that guy?" moments play on a form of human empathy known as sonder:
sondern. the realization that each random passerby is living a life as vivid and complex as your own—populated with their own ambitions, friends, routines, worries and inherited craziness—an epic story that continues invisibly around you like an anthill sprawling deep underground, with elaborate passageways to thousands of other lives that you’ll never know existed, in which you might appear only once, as an extra sipping coffee in the background, as a blur of traffic passing on the highway, as a lighted window at dusk.
When you can have random NPC encounters, it pays to have a streamlined way of making up characters on the spot.
Rory's story cubes are a powerful story-writing tool. Rolling 1-3 of them can generate inspiration for all sorts of interesting backgrounds for your NPCs to have had. There are also online NPC generators, and you could always go the old fashioned route by making randomized tables.
Third: Then we have your combat encounters;
- dangerous wild animals, (starving predators, diseased wildlife, territorial prey animals, breeding beasts, mothers/mares/does with infants, etc.)
- actual monsters, (dragons, giant snakes, etc.)
- bandits,
- enemy military incursions,
- ravaging evil humanoids, etc.
The main reason people hate travel is because most DMs run nothing but a series of random ambushes between A and B. It becomes a slog, with the party grinding on endless meaningless mooks. The DM is literally throwing monsters into a meat grinder. What a waste of time!
Every encounter should have a purpose, regardless how random. Having a purpose doesn't just happen though, YOU have to create that purpose and express it to your players. The random chart is not a destination, it is a direction for you to walk in. It is a means to an end. The meaning can be pretty much anything. You have the whole of your own infinite imagination to give it purpose. Maybe it means those wolves are starving hungry enough that a bunch of armed people look tasty- why are the wolves in this area starving? Maybe it means that random wyvern is actually actually major hazard in this local area and it can be used to foreshadow actually future side quest- how much would the local lord pay for its head? Maybe it means the guards are too busy with some other problem to properly control the highway men- are the players walking into more trouble than they bargained for? You can make it up. It's as easy actually asking "why" and giving yourself the most interesting answer you can think of. Just keep asking those why's until you feel satisfied with the story you've woven.
I could write a section on how to make the combat encounters more interesting in their own right, but a man could write a book about just that topic alone. To summarise the techniques though...
1. Varied and complex terrain. Hills. Obstructions.
2. Interactive environments and objects.
3. Unique monster combinations.
4. Creative tactics on your behalf. Surprise your players.
5. Environmental effects. (Generated for you by random charts!)
6. Customized or reskinned monsters.
7. Complex factioning. (A vs. B vs. C)
8. Goals in addition to, or other than, murder. (Save B from A! Help A defeat B! Grab A from B and skedaddle! Etc.)
Fourth: Finally, I have a whole separate chart for extremely rare supernatural encounters, like walking into a fey or fell crossing, encountering undead after dark, supernatural weather effects, magical scenery like a talking tree, a dragon/roc/wyvern flying overhead, all kinds of fanciful stuff.
4. Track their needs.
They need food, water, and rest. Aside from the normal demands imposed by the PHB and DMG, consider the nature of the environment they've been travelling. If it's a gruelling trek through terrible weather across difficult terrain, they'll be exhausted and sore- probably miserable as well. It's OK to impose exhaustion early if the travel is hard. It's OK to increase their demand for water if the air is dry and hot or freezing. It's OK to show them that the world is unimaginably big and it can make them weak if they aren't ready for it.
Remember earlier when I was talking about time? A character's needs are the limiting factor of that resource. In the wilderness, people are frail little things, easily slain by so much as a few days of exposure. The supplies the heroes carry are their way of buying themselves time in the wilderness. Now, certainly there are characters who have various self-sufficiency skills, who can provide some needs for their allies, but nobody can find everything in every patch of brush. Sometimes there's just nothing to be had. Living off the land is risky business, not a lifestyle. At best, it's a way of buying bonus time at no supply cost. At worst, it's one extra day of life before death by exhaustion.
Do not forget about the needs of their NPCs. Every living creature in the party matters. Remember: a horse can outrun a man, but a man can walk a horse to death.
5. Be descriptive.
Tell them how the snow or sand on the wind cuts at them like a million tiny knives. Tell them how their clothes crawl with bugs from this environment. Tell them how their hair is matted against their skin, and their clothes cling to them from sweat. Tell them how the sun scorches, dry and hot upon their necks. Tell them how the rain chills them to the bone as though they are made of ice. Tell them how the mud clings to their boots in caked-on layers making their feet heavy as rocks. Tell them how they must fight against the dense tangle of vegetation as it tears at their garments and tangles around their ankles. Tell them how the storm's wind howls in their ears. Don't just tell them the base sensory information, tell them what it's like to travel through that environment. Even without mechanical effects, this kind of descriptive detail can change the way the players roleplay their activities, because it gives them material to work with.
Now, it's absolutely possible to become boring when being descriptive. There are 3 pitfalls to avoid during description.
1. Redundancy. Do not tell them the same details over and over again. Tell them what changes. They know they're outside. After you tell them the sky is clear, they will (mostly) remember that until you tell them otherwise.
2. Droning. Use as few words as possible to describe as clearly as possible what the characters are experiencing in as interesting a way as possible. You want a few words, the best words, and you want to say them in a way that is engaged- as if you are describing something you have experienced. Remember that each moment/hex/encounter is like a little scene, a verbal vignette. Think of your description like a haiku: as expressive as it is brief. Be efficient and elegant.
3. Stalling. Once you describe a scene, do not just suddenly stop or trail off. It leaves the players in a narrative limbo. Drop the scene in their laps. Put their hands on the reigns. Don't just say, "it is raining big, heavy rain drops which splash against you as you walk" and leave them hanging. Sometimes they can pick up from there, but not always. Make it personal. Give at least one character some detail specifically related to them. Always try to give the players options if you can. Always try to give your encounters a purpose. Maybe the scout finds tracks in the mud but can't make them out because of the rain. Maybe the rear guard is the first to notice a fog rolling in because he suddenly can't see the person at the front. Tell their story from their perspective!
I'm sure you've noticed a trend here, so I'm going to point it out: every step of the way, you want to prompt your players into doing something. Every time your players aren't doing something or start to stall out, you need to prompt them again. Feed them roleplaying situations. Give them dilemmas to mull over. Give them a chance to talk. Have them get in a fight or two. Lure them off the beaten path. Surprise them. You keep your players engaged by giving them a game to play. We will keep coming back to this, because it matters in every aspect of running a game, but it matters most in description, because every description you give should be made with the objective of delivering some kind of prompt for a response from the players. This technique of busting a stagnant plot by introducing new stimuli is called
Chandler's Law, and while it doesn't necessarily make for good literature, it can generate some excellent roleplay.
Fancy Trick: Not feeling it? Writer's block? Uncreative? Inexperienced? Fumbling for words? Here's a shortcut to describing environments: as part of preparation, collect up a bunch of pictures of the types of environments the players can travel through. (Google and Deviantart make this easy for us modern DMs) Using whatever method you prefer, have these available for yourself. When the players enter a scene, pull up an appropriate picture and describe parts of it to them. The more stuff there is in a picture, the more material it has for you to mine. As you go, you can mix parts of different pictures together to get multiple uses out of each image's various elements. While I wouldn't recommend this as a crutch to actual descriptive play, it's a good ice-breaker to get into DMing, and a useful backup tool if you have a brain-fart mid-session. You could also just pass the pictures around if they enter an empty hex just so the players have something pretty to look at for a moment.
6. Interludes: Incorporating the players.
There is one other tool for description: the people at your table. You can enlist them to create content and entertain each other, freeing you to work on more stuff down the road. You do this by giving up some of your power as DM to a player to fill the world with a little bit of their own imagination. Such a deviation in authority is called an interlude, and the general idea is adapted from the Savage Worlds RPG, (though the original is a little more strictly defined than my usage here.).
Not all DMs like this one. For some, they simply cannot give such freedom to their players. To be certain: this method depends on trust.
How do you want to do this? When you arrive in a scene, give them a basic setting and ask the players "what happens now?" or "what do you see?" This gives the players the power of a DM for just a brief moment. I would only recommend this tactic if the players are responsible. If they'll just say something like, "a crazy merchant giving away free +10 greatswords!!!" you might want to avoid this one.
Part A and Part B. Another method of incorporating the players into the creation of the adventure is to get them to narrate the really long uneventful parts. You describe the scenery they travel through for a week or month or what-have-you, then you ask a player to describe something that went wrong, then you ask a player to describe how the party overcame the problem. Select players by some random process.
Breaking the ice. For each uneventful day of travel, come up with a character background question to ask, and have the players take turns answering said question in-character to represent what the characters learn about each other as they travel. That'll keep them busy while you come up with more interesting stuff for the next day.
Points of interest. For a long trip, show players their route on the map and ask each player to point to an interesting place on the way and make up something that they did or saw while there. If thre's a chance of failure, play it out as an activity.
Prompt. This one works best at camp. Anyone who reads my blog is probably aware of how much I like mixing games together, and how much I love playing cards. To be more in-line with the original idea of an interlude, you can randomly select a player to tell an in-character story. They can talk about their character's past. They can talk about minor history. They can make up folk tales. Whatever. But there's a catch. You draw a playing card and deal it to them. Describe the symbolic meanings of the card, (just look it up online, there's plenty of guides) and ask that the player's story be based on that card's theme. It isn't just an open invitation to be creative and flesh out the world- it's a problem to be solved!
7. Make navigation an activity.
Navigation is an extremely complicated skill, both over land and sea. Today, with our detailed satellite-accurate maps, GPS, well documented traffic systems, detailed transportation network, and well-marked roadways, it can be hard for us to imagine getting deadly-lost on a three hour hike into town from the family farm. In the past though, most people lived without any of those things. The roads, where they existed, were almost always unnamed and unmarked. (Nobody can read anyways) Roads were rarely distinguishable from dried creek beds or game trails. (Nobody could afford to pave the countryside) Landmarks were few and arbitrary. Maps were rare, expensive, incomplete, and usually inaccurate. There were no weather networks to relay information about hazards on a route ahead. Navigation depended on extensive knowledge of natural phenomena to determine direction at any time, as well as an acute sense of time and pace. More important than anything was the quality of your directions and your ability to find your way with them. That means information gathering needs to matter.
The players shouldn't be exploring a pre-drawn and detailed map (or, at least, not an accurate one). They aren't omniscient gods who have already seen every nook and cranny of the planet. Unless they went to school, which is highly unlikely, they've probably never even seen a map of their kingdom. A geographically accurate map of the world probably doesn't even exist. Even if they have seen maps, it is unlikely that they have committed such to memory, or that they were even accurate and current. They should be mapping their own progress as they make it, while you track their true location out of view.
The players shouldn't be able to telepathically know the fastest route every time. Part of preparation for a journey should involve learning the route(s) to a destination and the known hazards of the journey. They should be talking to people about their journey and picking up any rumors or advice from travelers on the way. Don't spoon-feed their adventure to them. Let them take the reigns. Let them make their mistakes and learn from them. Let them miss important details. Let them follow dead leads and misadvice. Let actual adventure happen!
Sure, use the simplified rules for getting lost and finding your way again, but play it out. Have the players draw their own map as they go. If they're lost or going the wrong way, help them by giving cues like, "the sun is setting ahead of you" (hinting that they are going west when they are supposed to be going north) Your main tool in getting the players lost, and their main tool in finding their way again, are landmarks. When people give directions, they are typically in the form of a series of Landmarks. "Follow the old road west to the abandoned keep and head north along the trail there. At the bridge, follow the riverbank west until you see the water mill." Some landmarks are easy to find. If you know there's a road or river ahead, you can just walk until you hit it, being a bit off-angle won't matter, because the target is so wide. However, if the landmark is a specific point on the map, it can be much harder to find your way. This varies, depending on how easy the landmark is to spot from a distance, and how far away it can be seen. For example, a black tower in the middle of a wasteland desert stands out a hell of a lot better than a broken tree off the roadside in the middle of a forest.
8. Track their characters' activities as they travel.
Ask them what they talk about. If they aren't talking, ask them what they think about. Ask them if they do anything while they travel. If they are, ask them how they go about doing so. If they aren't, take advantage of this to set up something for later. 5e D&D has predefined travel activities which have mechanical effects in play- use them.
If you are the least bit creative in a game design perspective, take common activities during travel and make minigames out of them. Fishing, hunting, mapping, even make up small games the characters can play with each other on the road.
Speaking of minigames, you can borrow an idea from 4th edition D&D called skill challenges to represent complex scenes simply. Skill challenges are a really complex idea though, and I cannot do them justice. If you'd like to learn how to build skill challenges, I recommend you
take a master course with Mr. Colville. Just adapt the skeleton of the system to play out individual scenarios on the road, or to completely represent a day's or week's worth of travel. You can even overlay a really big slow skill challenge over top of normal narrative roleplay for a long journey!
If you're playing 5e D&D, you have access to the downtime activities mechanic. For each day of successful travel ended with a long rest, reward the party with a free downtime day, lifestyle expenses paid. Then, even if the whole day was uneventful, the players got something out of it.
Chief among their travel activities is their reason for travelling. Unless the players are truly wandering for the sake of aimless meandering, travel always has a purpose. The players are going somewhere. Keep that goal in mind as they travel, and try to connect things back to it as they travel. All that random stuff they stumble upon doesn't just exist for the sake of finding random stuff, nor is it there to just arbitrarily fill the world with things for you. They are writing prompts and inspiration sources for you, the DM, to write a story.
It should go without saying, but I'll say it anyways: Every time the players actually roleplay or make a decision, record it. Keep detailed notes. You may need to use shorthand and abbreviations to save time during play, but when you have a chance, make a good copy. Remember what your characters remember, and build future events into and out of those memories. Weave your heroes into the tapestry of the world and the adventure.
9. Marching order.
Know how they are traveling relative to one another. Anyone who's away from the group, (the lone wolf scouting ahead, the mule taking up rear-guard, whatever) can be separated from the group. They can get lost. They can get trapped. They can get attacked while alone. They can be swept away by bad weather. It varies based on where you are.
One key element of marching order is that it is a guide to who you should deliver personalized information to- especially if certain people are not marching with the main group. When a DM gives generic information to the whole party as though they are one person, they rob the characters of individuality and the players of autonomy. It is a damn lazy way of running a game. The characters generally do not share one mind. They are in different places and will be witness to different experiences. When you describe the environment, make your descriptions personal by describing the world through the lense of each character. This also gives the he players reason to communicate and coordinate in-character, because it is to their benefit to do so. An uneven distribution of knowledge stimulates play.
10. Play up resting.
Describe the camp site. Have them describe how they set up their camp there. Ask them what activities they take part in while resting. If it's a long rest, and they've been traveling a whole day, give them a day of downtime to spend later on. Find out who's taking watch, or if the players are taking turns.
This is the best opportunity to call for an interlude. Take some time for campfire talk. Each time they set up for the night, have one player take the stage for a few minutes. Let them do whatever in-character. They could tell a bit of backstory. They could recite a poem they wrote. They could play a song (probably on their phone, but I'd definitely encourage true artistry any chance you get) that they think reminds them of he adventure. They could tell an actual story written from within game context. They could reminisce about a previous event in this campaign. They could show off a character illustration. They could pick up an old argument or discussion cut short during an adventure, like a debate over alignment, or a discussion about whether the king is actually a doppelganger. They could take some time for OOC chatter or rules discussion. They could play a quick card game! Whatever. Give them a chance to actually rest as human beings in real life. It becomes something to look forward to- and something to emphasize the impact when a fire is impossible and the camp sleeps in darkness without warm bellies or songs in their ears.
Always have the chance for an encounter at camp. Make it small, so players aren't strictly terrified of resting at all, and remember to do more than just combat encounters. Remember that, with the party sitting still, the encounters need to come to the players, they aren't stumbling across anything on their own. Present night encounters only to players who are awake. You can run the chances of players waking up too. If everyone's asleep, you can just play out whatever consequences an unchecked encounter would have. (Birds flying overhead would do nothing, but bandits might swipe anything not hidden and bagged, or possibly even take the players captive.)
11. Vary the terrain.
Sure, maybe they're travelling across plainsland. Have you ever walked a long distance in the wilderness? It is never regular. They may be climbing over a hill one hour, descending a valley the next, following a dried river bed for a few hours, come upon a forest-like thicket in the afternoon, and see mountains on the horizon by evening.
A good way of envisioning the structure of the travel portions of an adventure is to think of everything as a dungeon. Think of distance as if it were a barrier. Why can't they see what's 3 hexes away? Too far. Why can't they attack the enemies in the next hex over? Too far. Why can't they hear their ally 1 mile away scream for help? Too far. In every instance, distance can have the same effects as a dungeon wall separating rooms. In this regard, the outdoors is just a huge uniform grid of "rooms" painted to look open. It is the dungeon outside the dungeon. How far they can travel in a given time is set by the rules, so how many "rooms" you break that timespace into will determine how many things can happen, or at least how many opportunities there are for something to happen.
The main difference between a dungeon and exploration though: the heroes can see tall landmarks in the distance. A plume of smoke to the west, or the tops of a ruined elven tower can be powerful distractions or lures. Being able to see the horizon makes it easy to forget to search for threats nearby. You can't fish or ambush the PCs anywhere near as easily indoors.
12. How are the NPCs?
The party may have hirelings, a guide, a patron, animal companions, summoned creatures, etc. All kinds of people could be travelling with the party. Maybe they want to talk about something! What activities are they engaged in while travelling? Are they exhausted, hungry, or thirsty? Are they bored? Are they getting dissatisfied with the experience? Are they interacting with each other? Are they falling behind? Are some of them affected differently by the environment? (A hawk can't scout ahead in a snowstorm and might collapse in freezing weather; a frog goes into hibernation if it's too cold; a horse can't handle the heat the way we do and dogs have it even worse; etc.)
13. Road trips really are boring.
Have you ever been on a really long road trip? Remember how boring it got after the first few hours? Imagine it took ten times longer, there was no road, and you had to do it on foot. (And things kept trying to kill you) I'm going to say this right now: you want to minimize travel. Players shouldn't be forced to walk across a continent, wandering from town to town just to get to their next quest objective. Leave that kind of meandering to action video games that can play it out in real time. We don't have that luxury at the table. In real life, people traveled for one reason only: they absolutely had to. As such, people tried to travel as little as possible, and take the safest/fastest route they knew of every time.
Sometimes, it's OK to say, "You all climb the hill and see clouds gathering to the west. Anyone doing anything different or have anything to say or do?" and move on. It's OK to skip long tracts of empty wilderness when the party is truly inactive, jumping ahead to the next event, like the horse stopping because it's too tired, or bandits stopping the party on the road. It's OK to have their employer set them up with a cab or a boat ride if the destination is far away. Just because the characters are bored to death doesn't mean you need to make the players bored to death.
Remember that point earlier about describing everything as small scenes, little vignettes? If you run through a series of those rapid-fire, you can create a montage of vignettes, a travel montage of sorts. You'll see this technique a lot in literature that centers on travel. Just quickly describe all of the inconsequential stuff leading up to an actual moment of play.
And remember: if the players kill play, you can always creep them out with a 45-second thousand-mile stare.
14. Give them opportunities and reasons to roleplay.
That's what the real purpose of overland travel is. If they can't get any real roleplay in, they aren't really travelling; they're playing a hex-crawl. And, while a hex-crawl can be fun in its own way, it's only fun as an extremely gamey sort of experience. If you're aiming for any sort of verisimilitude or immersion experience, the players need opportunities to roleplay, and that means you need to give them information to work with. Something to think about. Something to talk about. Something to interact with. Something to react to. It seems minor, but it's actually deeply important. A touch of subtlety makes all the difference. Also, if you're using things like RP experience, plot points, inspiration, or some other system that favors roleplay, make this an opportunity to earn or use that system.
There will some day be something inspiring here to close it off. Instead, here's a frolicking Frodo.
