D&D 5E how to run long distance travelling without it sucking

Would LoTR have been a better story if "Frodo and Sam travelled for a month and arrived at Mount Doom"?

Along the way, Tolkien showed us a fair bit about the terrain of Middle-Earth, and also developed the relationship between Sam, Frodo, Gollum and Smeagol (politely skipping over the more intimate aspects of that four-way connection). The loving description of plant species which I've never seen, weren't as meaningful to me as they might be an Englishman, but it was a decent setup for the desolation of Mordor.

There's also seeing weird stuff without interacting with it, or at least without giving or taking damage, for example passing over the marshes where a huge battle had happened long ago.

Have the party overtake a convoy of pilgrims. Mention that one pilgrim is telling a story to others. If someone says that they listen in, have them make an Int (Religion) check... then tell the group a story from the Canterbury Tales.

Three months later, do a story which that Tale foreshadows - for example, a lost treasure, and the key clue is something they might remember from the pilgrim's story.
 

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If they are travelling from one known location to another known location you can simply say x number of days (weeks, so forth) have passed and you have arrived at your destination.
 

The essential question you need to ask is why the travel is interesting. If it involves exploring new territory (e.g. hex crawls), making it through dangerous terrain (e.g. deserts, water rations and sand storms), sneaking through hostile territory (e.g. avoiding attention of goblin patrols), or is with potentially hostile companions (e.g. putting down the brewing mutiny on your vessel), then the travel adventure becomes about that interesting characteristic. If you answer "none of the above", then the travel isn't interesting and you should narrate over the bulk of it, inserting an encounter (or two) if its appropriate for the world and the game session.

-KS
 

I think you need to tell us a little more about what you want on the journey. Decide how much challenge you want, and decide what you like. Don't repeat what you know you don't like.
 

What really destroys encounters while on a long journey is the hard coupling of days and long rests.

Unless all encounters are either cakewalks or incredibly deadly you really must do away with this idea.

Instead stipulate that you only get the benefits of a long rest once the journey is over (you've crossed the desert, you are on the other.side of the ocean, youve climbed the mountains etc)...

... and ordinary night rests provide only short rest benefits, if even that.

Then you have a situation where ordinary (weak) foes retain their function without becoming completely pointless.

It's a shame dnd have never understood that the frequency of long and short rests must always be left up to the adventure to stipulate.

What works for a dungeon does not work for other kinds of adventures.
 

What really destroys encounters while on a long journey is the hard coupling of days and long rests.

If it's easy to have a rest, then the journey isn't much of a journey. The territory should be perilous enough that any mechanically significant rest risks triggering an encounter or other hazard.
 


There is a problem I've run into: Rangers. Specifically that their favored terrain ability says "you can't get lost". Which makes for a very lame walk through the dangerous woods unless you do the following, which is what I did to my rangers(there were 3 at my table!): 1: the terrain is magical, by the book this overrules the "you can't get lost" feature. 2: the ranger is an idiot; by that I mean that I make them make a survival/nature check to determine if they are making progress towards their destination, or not. 3: The party takes over; this is easy: offer something to cause the party to disagree on what direction to take. The ranger might get outvoted and off into the woods they will go!

So long as you use that sparingly... If the ranger is never able to be a capable woodlands guide like they're supposed to be, it makes the player feel like a chump. How would it have looked if Strider got lost half the time?
 

Run it like you would a dungeon; break the trip down into "legs", at each leg create an event that can happen, stuff like bad weather, breakdown, bandits, some one in distress, another traveler, nothing.

The road is a passage, the events are rooms. Think about what people do to pass the time on any trip, at night a bard will sing and tell stories, you may meet lumber jacks or tinkers, hunters and such. People will ask road conditions in passing.
 
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Some good ideas here. I think this may be an area where leveraging Group Check mechanics is a good idea:

a) Pick some standard roles that would apply to such a travel. Dungeon World uses Quartermaster, Scout, Trailblazer. Those are quite good I find. Perhaps if more than one person is managing provisions, navigation, or recon, you could have the highest person roll with advantage.

b) Pick relevant DCs for the group to roll against.

c) If 50 % or more pass, they arrive and expend the normal amount of expected provisions, etc (that might be just ticking off some gold from each player's stash).

or

d) If 50 % fail, an interesting, dangerous setback occurs along the way. This could be:

* a geographical hazard
* an encounter with relevant monsters or a lair creature
* the PCs getting separated
* the PCs getting lost
* weather or climate related exposure
* you might take this opportunity to introduce an ominous new threat or escalate an existing one

Regarding tangible fallout on the PCs mechanically, this would be a good area to introduce the Exhaustion Track and/or charge them n number of Hit Dice apiece. Then they would have to roll their Group Check again to get to their destination (or incur more complications if they fail again!).

You may want to impose the condition of no Long Rests until they reach civilization or make them earn a Long Rest mechanically.

The math on group checks can get a little odd though if you don't adjust the DCs downward when more characters are involved in the check. For the sake of simplicity, let's say the average bonus for the PCs is 0, the DC for the task is 15:

Two characters (one doing the task with the other taking the Help action) has a 51% chance of success.

Now if we go with 3 PCs and a group check where 2 or more must succeed, the odds of success drop significantly to 22%.

If we go with 4 PCs (2 must succeed), the odds are a more favorable 35%, but still not as good as one character with one helping.

For 5 PCs where three must succeed, the odds are only 17%.

Players that know the math (and have an odd-numbered party) might just try to avoid making group checks like the plague which I'm sure was not the intent of the mechanic. Because I always have four players, my general rule of thumb is to drop the DC by 5 for a group check of 3 to 4 and rule that a fifth person (like an NPC) isn't of any help and possibly represents that one too many cooks spoiling the broth.
 

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