Rolling for Monsters Wrong
Travel encounters first came to my attention though the 'Encounter Tables' included in every Dungeon Master's Guide that I can remember. Always a table of monsters organized by biome and challenge rating, I was genuinely under the impression that random monsters needed to pop out of the woodwork every hundred to brawl the party on the road, like a Pokémon encounter in the tall grass, or a Final Fantasy encounter while riding a chocobo. But actually putting it to the test, I quickly realized that it ate time at the table, and contributed next to nothing to the session, as I nervously twittled my thumbs, hoping that I would have time to get to the real encounters of the evening. So why do these exist, and how should your table handle traveling in general?
Always Take the Scenic Route
No Dungeon Master that handles the party traveling between locations correctly will complain that his players aren't immersed in the world. After all, your players can't care about the world if they don't spend time in it. Your encounters that take place on the road provide a valuable opportunity to highlight the everyday struggles of the small villages and quiet hamlets of your campaign world, along with giving your party an opportunity to stumble across things they didn't expect. It's these little insights that happen mid-adventure that create a living, breathing campaign world for the players.
Travel time is also important because of momentum. Shuffling the party back and forth from major world-at-stake quest to major world-at-stake quest might be good for building one exciting climax, but you can't really raise the stakes any higher after that. If you take your time getting between places and provide some adventures along the way, rather than smash-cutting past travel sequences, you can provide plenty of fun little quests between the really big ones that happen at the destinations.
Why Not Just Teleport?
A popular method for sidestepping the problem of traveling in D&D is just to make teleportation cheap and plentiful, or to simply ignore the process of traveling entirely and resolutely declare 'You Arrive!'. In either of these scenarios, every city might as well be next door, and your campaign world just ends up feeling small and inconsequential. After all, there's no way to gauge scale when you just appear where you need to be to continue the quest.
Moreover, this also reduces the types of encounters you can present the party with. There's bound to be fewer ambushes or chase scenes if you never put the party on an open road. You'd be surprised the battles you can pull off with a raiding party of gnolls and a spice caravan in the middle of nowhere.
Ditch the Encounter Table with Mini-Quests
If there's one thing I've learned, it's that a mini-quest is the best way to drag your players down a rabbit hole. Now, using a collection of short quests that can be drawn out of a hat as needed is something that needs an article all on its own, but it's 100% the way I handle travel encounters.
We'll go into the details about how to write these another time, and how to make sure that they do the most to reveal the intricacies of your campaign world, but for now imagine that you have a list of short quests, each with a plot hook, a combat encounter, an exploration encounter, and no less than two NPC or environment-puzzle interaction encounters. These mini-quests are short (no more than a couple hours of game time), and highly dependent on having a catchy, interesting hook to drag the players in. These hooks are what we use to replace the typical monster encounter table.
Compile all the plot hooks that can be casually encountered on the road, far from a city, (be it on the road itself, in a small rural hamlet, or while you travel through a neck of the woods) on a small table, and just roll for them. You get to flex some improvisational muscles (the DM's most important skill) and be as entertained as your players by the turn of events. Last but not least, once you've run a few encapsulated mini-quests on the way to somewhere, it feels like everyone has really traveled somewhere and experienced the world along the way. Immersion accomplished.
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