5 Steps to Creating Epic Side Quests

I love side quests. I have always wanted a bumper sticker that says, “I brake for side quests.” I know I am not alone. Who else has spent hours upon hours completing every random side quest available in a video game before even starting the main storyline? Don’t be ashamed! Side quests are awesome!

When done correctly, side quests can be a work of art. They help players develop skills and gather the information and resources they will need later. Heck, they can even be amazing stories in and of themselves! Side quests allow players to explore the world and people around them in short but meaningful ways.

There are few games that provide both the time and format, and even encourage the use of side quests, such as Dungeons & Dragons. In these games, there is a whole world of possibilities (literally!) and the only limiting factor is the size of your imagination.

But with all this freedom comes the daunting responsibility of the DM to try to connect all the dots.

How do we, as DMs, create these and lead our players to the kinds of side quests they will remember? How do we create truly epic side quests?

To help you develop your own epic side quests I have created this 5 step guide. This is not a pre-made side quest, this is a guide to help you create your own unique and fun quests, tailor-made for your party.

Step 1: Think About Purpose

There is a difference between a random encounter and a side quest. That difference is purpose.

A great story, no matter how long or how short, has a purpose. What is the purpose of your side quest? No matter how simple or silly your quest, it should have a takeaway. A side quest of rescuing a child’s kite from a tree could have the purpose of reminding a jaded party that there is still innocence in the world that needs protecting.

A side quest of healing a village racked with a horrible disease could awaken the party to the realization the mages’ guild is experimenting with ancient, evil magic.

Perhaps the purpose is as simple as creating bonds and trust within the party or creating ties to a local village/area (which may or may not be destroyed by a dragon later.) The point is, a good quest accomplishes a purpose. Here are some other purposes your quest could accomplish:

  •       Acquiring a rare/unique item
  •       Gathering resources (show me the money!)
  •       Gathering Intel
  •       Lifting the mood
  •       Taking a break from constant combat
  •       Developing characters and bonds
  •       Setting up a new plot

Whatever the purpose, your side quest should provide the party with something meaningful, or it will just be a waste of everyone’s time.

Take Away: There are many purposes to side quests, make sure you know what your purpose is.

Step 2: Decide How Long the Side Quest Should Be

The length of your side quest will depend largely on your purpose. The search for a rare magical item may take several sessions, but side quests do not have to be long to be impactful. A mini-quest can be as short as 10-20 minutes but, if done correctly, the impact will last the whole campaign.

Example: My group was on their way to a Drow city on the other side of a mountain range, far beyond the reach of civilization. At the base of the mountains was a small village, their last stop before entering untamed wilderness. Up until this point, the group of mixed race adventurers hadn’t had great interactions with the common folk, to the point that they were beginning to discuss not completing the quest and saving this world.

When they entered the village, the people avoided them, mummering under their breath, everyone except one small boy. He stared at them, wide eyed and clearly enamored. As he stared, a gust of wind pulled at his kite, ripping the string from his small hand and taking the kite high into the sky.

He began to cry. The group, naturally, rushed to his aid, promising to locate his missing kite. The boy beamed and the side quest began.

This mission only lasted about 20 minutes, but my players still talk about it. Mostly because the quest ended with the half-orc rolling a natural 1 on a low dexterity check to pull the kite from the tree it was stuck in, thus tearing the kite in half as he tried to dislodge it. The whole group had a lovely ceremony for the kite and shared a moment of silence as the Dragonborn used his breath weapon to send the kite up to kite heaven in flames…before he remembered he had the mending spell.

The group then played a rather intense game of hide and seek before escorting the boy home.

 This short and silly side quest  served two purposes:

  1. To remind the group who they were fighting for
  2. To give them a moment of lighthearted fun before, what I knew was to be, a long, hard battle ahead.

     Take away: Side quests do not have to be long and intricate to be deeply meaningful.

Step 3: Consider Campaign Tie-In

Although a side quest can be completely random, the best side quests have some kind of tie-in to the main story line, even if your players don’t realize it…yet. A character or item from a side quest can show up later to save the party in their hour of need, or becomes vitally important to the success of a mission.

I can tell you from experience that players love it when a seemingly random event or useless item is woven into the story line. Do this a couple of times and I guarantee your players will be on the lookout for side quests and taking notes on the NPCs they meet along the way.

Take Away: Tie NPCs, events and items into the main story.

Step 4: Create Player Buy-In

Why should your players care? If you can’t answer this, then don’t expect your players to take the time and energy to jump through your hoops.

There are lots of ways to create buy-in, the simplest and most obvious is money. If your group is strapped for cash, they will most likely do whatever promises gold.

However, this is an extrinsic motivation that will likely not last long. Don’t rely on the promise of gold to create buy-in every time. Eventually, your party will be too rich to care, and if they do need the money, that is all they will be interested in. No names, no conversations, nothing but gold.

Some better ways to create party buy-in are to appeal to your player’s backstories, bonds, or flaws. Each of these creates a deeper motivation that will ensure players complete the quest and do so in a timely manner. How you appeal to these will depend on your players, but every player will have something you can use against them. Are they a gambling addict? Perhaps they have a tragic backstory involving losing their parents (who doesn’t?) whatever it is, use it to create buy-in.

Take Away: Not all that glitters is gold. Create player buy-in through the use of emotion.

Step 5: Create Memorable NPCs

The heart and soul of a side quest! Creative and fun Non-Player Characters can make a side quest truly epic, and you don’t have to be a voice actor to bring them to life!

It is more important for the people of your world to feel like real people than it is for them to have a unique voice. Here are some questions to ask about your NPCs

  •       What are his/her flaws?
  •       What do they want and what are they willing to do to get it?
  •       What are their bonds?
  •       What has their life experience been thus far? Are they innocent or jaded?

This are just a few questions that will help guide you in the creation of NPCs. If you are looking for more information on creating NPCs, check out this article on Creating Unforgettable NPCS.

In the end, it isn’t about how clever your stories or how detailed your character descriptions are, it is about making sure the players have fun. Side quests can be the times when your really “let your hair down” so to speak. They can hit the players hearts, make them laugh, make them cry, or just let them try that one ridiculous spell they have been so excited to use.

Regardless of the type of game you run, the kinds of players you have or what you’re a looking to accomplish, if you follow these simple guidelines, you will create epic side quests your players can’t get enough of.

Until next time,

May your game have advantage, my friend!

-Halfling Hannah

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