Making Milestones, Part One: Trailblazing

This post is part of a two-part series on Milestones, focused on using this alternate method of rewarding Experience Points. In part one the idea of Milestones as presented in the DMG is talked about at length, especially regarding how it can help DMs influence how the game plays, and an alternate approach is given. In part two the alternate take on Milestones is expanded upon as a Variant Rule that provides characters a source of Inspiration and Experience.

There are many things to enjoy about fantasy roleplaying; some people are into it for the escapism, some for the creative exercise, some because they get a kick out of exploring the fictional world that’s being spun by the person behind the DM screen.

Usually if D&D is the game of choice everyone accepts that the core reward currency – loot and experience points – are mostly gained through combat or deadly challenges, and this works in large part because experience ties into levels which can give everyone a rough idea of what the characters can survive poking with a sharp stick (metaphorical or literal).

But D&D’s 5th edition also explicitly calls out a number of alternate progression mechanisms, for groups that want to reward different behavior or embrace a more narrative approach to leveling up. One of these is the Milestone approach, which I believe is a pretty great idea because it gives the DM a loose framework for rewarding XP for whatever is important to their game.

and because it can help them reinforce the sort of themes or play they want at the table, in a way that makes it clear to the players (or reminds them, as it’s always best the DM and players be on the same page about what sort of game everyone is looking for) what sort of behavior will get their characters rewarded.

Milestones By The Book

On page 261 of the Dungeon Master’s Guide there is a brief discussion of milestones, an alternative or additional way of providing characters Experience Points; you hand out XP when they hit important parts of the adventure. The recommended allowance of points is either equivalent to a Hard Encounter (for a major milestone) or an Easy Encounter (for a minor milestone).

I won’t reproduce all of that book’s advice, but I want to build on it.

Based on the advice in the DMG, a small starting adventure’s milestones might look like this:

  • Minor: Discover the Deacon’s slowly being corrupted by harrowing dreams.
  • Major: Handle the outbreak of violence among those who’ve fallen ill.
  • Major: Convince the Deacon he has been compromised, or defeat him when he becomes fully possessed.
  • Minor: Discover the broken mirror, rotted fish, and dead birds that point to the shepherd.
  • Major: Defeat the full incarnation of the plague-demon when confronting the shepherd.
  • Minor: Discover the dark-magic letter from Triboar on the shepherd’s body and the letters to the Deacon from “Brother Samwell” at the hermitage outside Triboar are in the same handwriting.

Now what these tell us is not only that the DM has presented the characters with a mystery to solve, one that has a number of clues and only a few combat situations built in, but that the scenario is a bit dark. Their approach was to mark out the finding of certain clues that are required for the story to move forward, and other confrontations that these clues led to, for reward.

But what if the Milestones were used to reinforce the themes or focuses of the game?

If the scenario going for a “The Touch of Evil in a Small Town” feel then perhaps you could include milestones like:

  • Minor: The group either demands the townsfolk’s hostilities cease on threat of violence or convinces the locals the party is not to blame for what’s happened.


  • Minor: The party realizes that the disturbing dreams they’ve been having aren’t their own, but belong to someone local to the town.

These not only prompt the DM to use any particularly nifty narrative tricks they might have come up with, reinforcing the feel as much as any plot, but allow that the players may take more than one approach when presented with these scenarios.

Similarly, if the intent is to reinforce the mystery aspect of the adventure – without relying too heavily on players asking the perfect questions or making the right Investigation check – one solution is to create milestones that remind the DM to provide the players with multiple paths to their solution.

  • Minor: It’s discovered that the dreams the party has been having are, when put together, are parts of one whole demonic nightmare from the Deacon’s perspective.


  • Minor: The party discovers 3 of the 6 clues that indicate the source of the corruption is the shepherd or his fields. If they collect more than 3 they almost certainly know it is the shepherd himself.


  • Minor: A member of the party decides to try and treat the sick, quickly discovering that the first to fall ill lived on the south side of town.

It’s even possible to include optional, but helpful, discoveries in this manner so that they provide a non-XP reward:

  • The players discover the old shrine to Deneir and may take the small stone bowl with the glyph carved on the bottom that wards against disease and rot. This also provides Advantage to notice the glyph on older houses in the village.

Whatever the approach, just remember that when a DM adds milestones to the game in this way – either to replace or supplement traditional sources of XP – they are making choices about what sort of actions and behavior they reward at the table.

Player-Facing Milestones

Another, very different, approach is to create your own personal little XP levers and put them in the hands of the players (in a style which has been directly inspired by the amazing superhero game Marvel Heroic Roleplaying). I am going to talk more about this, at length, in the next post on Milestones but here are the basics for those who are interested in just the core concept.

The DM has their plot, their clues, their NPCs, and their encounters. That part doesn’t change. Instead the DM comes up with a few sets of milestones, Paths, that act as small character arcs or ways of interacting with the adventure, and allows the players to pick one.

Each of these Paths has three milestones: the first can be completed multiple times a session but only when it makes sense, the second can only be completed once a session, the third can only ever be completed once. After the third milestone has been triggered the Path is finished and a new one must be chosen.

In a given Path the rewards for completing a milestone are:

  1. An XP reward equivalent to completing an Easy Encounter.
  2. An XP reward equivalent to completing a Medium Encounter.
  3. An XP reward equivalent to completing a Hard Encounter.

The format of a Path changes based on whether its focus is on a character’s role or on a character’s priorities in regards to the adventure. Generally, though, Paths take the following form:

1 – An action that makes the character’s personality or priorities clear to everyone present. It should be something that could be done a few times, and adds to the atmosphere of the story or dynamic of the characters.

2 – An action that shows doubt, a lapse, or otherwise seems to run counter to the larger goal of the Path. It should be something a character will have to answer for, or think about, and should tie directly into the plot or themes of the adventure.

3 – A major choice that marks the end of the Path and will change the way others view the character or how they view themselves. This is deciding if the villain dies or is forgiven, if evil will be punished or overlooked for a larger gain, if the personal ideals win out over the promises made. It makes or breaks the Path’s narrative or character arc.

Just note that, at each step, this is something that the character does. This means that they’ll need the opportunity to complete each of them, and if a milestone or entire Path is sitting unused for too long it may be time to revisit that part of the adventure or exchange it for a new one.

Examples (based loosely on a little-known fantasy book):

The Ring-Bearer The Secretive Guide
1 Attempt to explain the difficulties and pain of carrying the cursed ring to another member of your group. 1 Declare that you know, personally or by reputation, all about your destination. Even if you cannot remember anything useful.
2 When you voice open mistrust of, and lash out at, those who are helping you due to the influence of the ring. 2 Refuse to directly answer an important question, in a situation where doing so could cause injury or imprisonment.
3 You either finally resolve to destroy the ring no matter what the cost, or attempt to keep it for yourself. 3 You decide to lead the group through a place of extreme hazard, or appoint another as the better guide.
The Conflicted Soul The Pilgrim
1 Swearing by whatever you hold sacred that you will act on someone else’s behalf. 1 Describe at length the glories of a place you have never been but wish dearly to visit.
2 When you attempt to usurp someone else’s position or role, blaming the situation on conflicting responsibilities. 2 When you discover a new location and admit that it may be greater than one of your storied destinations.
3 You either openly attempt to betray an oath you’ve made, or allow yourself to be seriously wounded in order to keep it. 3 You either put the entire party at risk to visit one of your favored destinations, or declare they were likely to be disappointments.

It may take a while to get the hang of it, and groups will have different feelings on how specific or vague the Paths for an adventure should be (mostly in terms of comfort level with mechanics that might imply how a player’s character feels about things). This last point is, again, why making each milestone completion based on the intentional decision to act by the player is so important.

I’ll be talking more about this type of approach, and providing plenty more examples, in the next Making Milestones post!


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