Side quests can bring players to new conflicts. Modified image, original by Midjourney.

How to Create Compelling D&D Side Quests

When we’re playing Dungeons & Dragons, the main story arc is the heart of the game. However, D&D side quests can add depth and richness to our campaigns, making the world feel more real and increasing our players’ emotional connection to the game’s characters and setting.

Let’s make a side quest together. In this article, we’ll go through the process, step-by-step, to create a side quest that will keep our players engaged and eager for more.

Disclaimer: All opinions expressed here are my own. This post may contain affiliate links. At no additional cost to you, I may earn a small commission.

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Side quests can bring players to new conflicts. Modified image, original by Midjourney.

A Step-by-Step Guide to Creating Memorable D&D Side Quests

We’re going to build a side quest together, using the method below. Substitute out your own game’s details or interesting ideas that you have as we go along, and you’ll have an entire side quest or encounter ready to go by the end of this article. Feel free to just take mine as is, too!

As we go through these steps together, one of the main things to keep in mind is your players and your table. My players may be very different from yours. What I come up with may be a total snooze-fest for your group. Keep your own game’s dynamics in mind and tweak your quest idea to make it something you know they’ll find irresistible.

Let’s get started.

Your D&D side quests can have fierce battles, new monsters... or just conversation. Modified image, original by Midjourney.

What Do You Need, Dungeon Master?

Why are you making this side quest? Here are some possible reasons:

  • For fun, to mix up the game a bit. Something fresh for your players to engage with
  • You want to show off a new puzzle, NPC, shop, or other small game element without forcing it into the primary story arc
  • You want to plant “hooks” for the next potential story arc(s)
  • You want to diversify the approach to the primary campaign. Perhaps the players are seeking a specific item or person tied to the story in a secondary way, and they are checking out a lead.
  • You want to enrich the world they players are in, to make it seem more diverse, interesting and relevant
  • Lots of other reasons, but do have one in mind.

Once you know WHY you’re creating the side quest, you can build backwards from there.

D&D, or Dungeons & Dragons, is one of the most popular TTRPGs in the gaming world! Delight your players with dynamic sessions, exciting one shots, and loads of fun NPC surprises! A D&D game is a great way to brighten up your week.

Building a Sample D&D Side Quest Example

DM Need: For my example, I will say that I am making this side quest to enrich the world the players are in. This is usually why I make side quests available; I want my players to feel like they are in a thriving, vibrant world full of opportunity and conflict.

Your D&D side quests should bring players to new locations, if the story permits it. Modified image, original by Midjourney.

Consider Your Setting

Your campaign’s setting is a rich source of inspiration for side quests. Think about the different locations and cultures in your world, and consider how they can provide opportunities for side quests. For example, a side quest in a seafaring campaign could involve navigating treacherous waters or fighting off a group of pirates. It could also feature a lovable, but mercurial and terribly dangerous shark acting as a “child king.” But we do like weird NPCs at my table.

A side quest in a city campaign could involve navigating the political intrigue of different factions or investigating a series of mysterious disappearances. You could even have them solve a murder mystery or incorporate components from a one shot that you’re interested in.

My table loves political intrigue. I was nervous to run a “wheels within wheels” political campaign when we began, but as DMs do, I adapted. Don’t be intimidated by something you’ve never done. It’s a game. Dive in and have fun with it.

D&D, or Dungeons & Dragons, is one of the most popular TTRPGs in the gaming world! Delight your players with dynamic sessions, exciting one shots, and loads of fun NPC surprises! A D&D game is a great way to brighten up your week.

Building a Sample D&D Side Quest Example

Setting: My current primary campaign is set in Waterdeep on the Sword Coast. I want my players to feel like Waterdeep is a real city, thriving and vibrant with many unusual denizens and something interesting around every corner, but I also want them to leave sometimes. I’m going to start the side quest in the city, and have it involve at least one new NPC, because my players L O V E meeting new weirdos in town. The quest will require them to go to a new location outside the city.

I’ll come up with the details for the NPC either organically as the quest evolves in my mind, or randomly later on if it’s not as important to the quest.

I’ve chosen to have them transport an unusual mimic to a Mimic Museum. It sits just outside the town of Orogoth. I’ve turned Orogoth into ruins that have been overrun by a thunder of black dragons. My party will not want to cut through this city.

The museum inspiration comes from Tom Cartos. It’s a great idea!

Be creative in the creatures and people your players get to meet. That's half the fun. Modified image, original by Midjourney.

Make it Relevant

A compelling D&D side quest needs to be relevant to something already present in the game. This could also give you a very natural hook to engage your players in the story. If it’s totally random, your players may read unnecessarily into details, trying to find meaning.

It could be an offshoot or spinoff from the primary campaign:

an old villain reappears, terrorizing a small town, Sharkey style

It could be tied into one of your player’s backstories:

a mysterious note arrives from previously missing mom or dad to one of your party’s characters, because I bet you have at least one orphan at your table….

A beloved NPC is in danger:

the tavern keep you love joking with every time you pass through this town hasn’t been to work in two days. The only clue is a discarded wine skin with orc blood inside

Relevance = Emotional Investment

A connection like this will help your players feel invested in the side quest right away. It can also tie into the bigger picture, if you want. For example, if your main quest is to defeat a dark lord, a relevant side quest could involve gathering information about the dark lord’s weaknesses or recruiting allies to help in the final battle.

A side quest that ties into a character’s backstory can provide them with a meaningful opportunity to explore their personal story arc. This opportunity should not be downplayed; the more your players are invested in their characters emotionally, the more engaged they will likely be in the campaign.

D&D, or Dungeons & Dragons, is one of the most popular TTRPGs in the gaming world! Delight your players with dynamic sessions, exciting one shots, and loads of fun NPC surprises! A D&D game is a great way to brighten up your week.

Building a Sample D&D Side Quest Example

Relevance: I’m not going to put an NPC in danger this time, because we’ve had that happen a few times recently in different scenarios. I’d like to incorporate a character backstory, because it’s been a little bit since we’ve done any work with that. I’m going to pick the player at my table who seems least interested in their character to see if I can help increase their engagement.

As the hook for this quest, I’ve chosen to use the soul coin one of my players carries that holds the soul of their old mentor.

Interesting NPCs can really light up a side quest. Modified image, original by Midjourney.

Increase the Stakes

High stakes makes everything more interesting. Who here loves gambling?

There should be significant consequences for success or failure. This does NOT mean only a TPK (total party kill). It can be lots of things, some of which are only based on roleplay, and should be judged on whether your players enjoy that or not. For example, maybe a character loses an important memory, or loses someone important to their backstory.

Stakes can come in the form of time limits, moral dilemmas, or threats to the party or NPCs. For example, a side quest that involves rescuing a kidnapped NPC may have a time limit before the NPC is killed, sold, or turned into an evil mage’s lab rat. Alternatively, a side quest that involves a moral dilemma, such as choosing between saving a village or saving a group of refugees, can add depth and complexity to your campaign.

I love these types of dilemmas. Which one means more to you, players? It is so emotionally powerful and engaging to have them choose.

D&D, or Dungeons & Dragons, is one of the most popular TTRPGs in the gaming world! Delight your players with dynamic sessions, exciting one shots, and loads of fun NPC surprises! A D&D game is a great way to brighten up your week.

Building a Sample D&D Side Quest Example

Stakes: Failure in this quest means the mimic will not share information with the player about their mentor. It also could result in a TPK, in this situation.

Puzzles can be for a prize, or even be as dramatic as saving a life. Modified image, original by Midjourney.

Add a Puzzle

Adding puzzles and challenges to your D&D side quest can make them more engaging and memorable. These can be anything from riddles and logic puzzles to combat encounters that require creative problem-solving. A side quest that involves infiltrating a guarded fortress may require the party to use stealth, deception, or even disguise to gain entry. A quest that involves navigating a labyrinth or solving a complex puzzle can add an element of mystery and intrigue to the session.

Usually, this is when a lot of the details of my story start to surface. I want my players curious and trying to figure out what’s going on, so this is when I will start to add mystery to each part of the quest, if I haven’t yet.

D&D, or Dungeons & Dragons, is one of the most popular TTRPGs in the gaming world! Delight your players with dynamic sessions, exciting one shots, and loads of fun NPC surprises! A D&D game is a great way to brighten up your week.

Building a Sample D&D Side Quest Example

Here are the puzzles I’m using:

Puzzle 1: How to talk to the Mimic

The mimic is unique in that it will have a conversation with the players, instead of immediately trying to eat them. Players will need to figure out a way to communicate with this creature.

They will learn the mimic used to be a chain devil, and was cursed by a higher devil due to a broken agreement. This creature knows about soul coins and can provide some details about my PC’s backstory.

Puzzle 2: Transporting the Mimic

The mimic will agree to divulge information if he is transported to a mimic museum he has heard about. It is a museum full of treasures that are actually mimics. He says he will be less lonely there, but he has a list of specific requirements to be transported safely so he isn’t tempted to eat the players during the journey. These requirements include an iron chest, two locks with two different keys held by two different party members, and a host of other requirements because he is fancy.

Players will need to figure out the best way to transport this monstrosity without drawing unwanted attention.

Puzzle 3: Find the Museum, Avoid the Dragons

Players will need to locate the museum based on loose directions from this creature, and avoid Orogoth at all costs. Of course, I will be waiting for an opportunity to make them feel they may need to approach the city, or make it desirable for some reason. It won’t be a requirement though, because it is too dangerous.

Everyone loves getting treasure in D&D. Modified image, original by Midjourney.

Provide Rewards

Will your players actually do things without a reward? Mine only occasionally do this — but they usually ask for some compensation once a task is complete, if nothing is offered up front.

Rewards can be anything from treasure and magic items to experience points or unique abilities. Rewards help your players feel like their efforts are being recognized and also provides motivation for future side quests.

A D&D side quest is an opportunity for something a little different. Modified image, original by Midjourney.

Final Sample D&D Side Quest Overview

Okay, here’s the complete overview:

DM Need: I am making this side quest to enrich the world the players are in. They find a mimic hiding in an old closet in their tavern. It was living in the dilapidated structure before my players owned it.

Setting: I’m going to start the side quest in Waterdeep, but have them leave the city. They will transport the mimic to a mimic museum on the outskirts of a ruined town overtaken by dragons.

Relevance: I’m incorporating a character backstory. The mimic can tell them about the soul coin one of my players carry.

Stakes: Failure means no information is shared, or possibly a TPK.

Puzzle: The players will need to transport the mimic safely, locate the museum with limited information, and possibly navigate around a ruined city filled with dragons.

Reward: Information plus whatever they can find in the museum that isn’t a mimic. I will plant a couple of things for them to find, depending on how they handle the situation.

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Closing Thoughts

That’s it. Coming up with compelling D&D side quests is a crucial part of building a rich and immersive Dungeons & Dragons campaign. By making side quests relevant, creating stakes, using your setting, incorporating puzzles and challenges, and providing rewards, you can create side quests that your players will remember long after the campaign has ended.

The entire process doesn’t need to take more than a few minutes, but of course as Dungeon Masters we love to embellish the details — this is half the fun. I’d love to hear about any side quests you’ve developed in the comments below. Happy questing!

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Love, Malice. I hope you enjoyed the article! I'm here if you have any questions. Feel free to leave a comment below!

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