Ah yes, the side quest. Proverbial bastion of endless possibility, and a break from the doldrums of the epic, world-saving quest or single-minded direction of the campaign thus far. We all use side quests, and we’ve all taken them. So how to get the most out of them?

I. Start With Why

I start by asking why I want particular side quests in my campaign. Side quests are great, but part of using them well is knowing when to use them, and why, and refraining from using them at times. I’ve listed several good answers to the question below, but the list is far from exhaustive. However, if I can’t answer the question with a compelling reason, perhaps sticking to the main plot is preferable. After all, that is where the main action is, and many players enjoy having that sort of driving purpose.

The Sub-Par Side Quest
The bad side quest is one that is simply spinning its wheels. It doesn’t have a strong “why.” You don’t want the campaign to be on the same path the entire time, so you fire up a pre-made one-shot or invent something on your own, and dangle the plot hook to your players. It might go well, but it’s a footnote to the campaign, not a compelling addition to it.

And at worst, it slows momentum or doesn’t match tonally with the rest of the campaign, thus detracting from the full experience.

II. The Player’s Perspective

Players don’t know what is and isn’t a side quest oftentimes. This seems obvious, but it’s easy to lose sight of that from behind the GM’s screen. We see all the strings attached to the plot. They don’t. With that in mind, some considerations:

Embedded Side Quests
I ran a brief campaign that had a fairly contained story, albeit in a city-wide sandbox. I dangled a few larger hooks shortly after the PCs arrived. A couple seemed far more obviously “side” quests. They were, in fact, simply different entry points into the same main story. But baked into each were sub-goals. So, for example, the corrupt circus leader had information on the mystical creature controlling the city’s leaders (main quest), but the circus was also involved in thieving, blackmail and far worse (side quest). They knew bits and pieces of the side quest from the hook, but not that it would also lead them back to the main quest. So the main quest could be resolved without shutting down the circus, but it presented another possible goal for the players alongside the main one.

The Quantum Side Quest
For more adventuresome GMs, a variant of this is where you throw multiple hooks at the players, let them choose 2-3, then retroactively make the one they’re most interested in tied to the main plot. The others you can resolve, but they become the actual side quests, not protracted story arcs. This is not to mislead the players, but rather to give them a chance to be the ones to decide where the meat of the plot is, based on their collective interests and actions.

III. Compelling Side Quests

Here are some reasons I’ve used that I think make for compelling side quests.

A. Flesh Out the Setting
Are you playing in a new setting? Or with new players? Or you love the setting but risk it seeming generic if you focus too much on plot? Bringing a setting to life is an eminently valid reason for side quests.

Case Study: Waterdeep: Dragon Heist is in the center of a fantasy metropolis that could support hundreds of sessions worth of play for any group. So when I ran it, I introduced both a job board at their home tavern and several local newspapers that the party could subscribe to (which I had printouts for). Each had numerous side quests, including (but not limited to) mutated bug infestations, investigating the theft of a family heirloom, competing in local sporting events, attending a public masquerade, and speed dating. Nearly all of them were simply to add flavor to the setting. I found a couple small ways to tie them to larger events, but the purpose was to bring the city to life. The campaign was better off for it.

B. The Player’s Journey
It can often be hard to incorporate a character’s backstory directly into the main plot, depending on how unrelated it may be to the backstory. For this reason, it can be good to find stopping points in the main quest, at which point you can tug one of the players in a more personal direction. I often get into the mentality that the main quest is on some sort of timer. But you control the pace of events. Even if this side arc doesn’t ultimately tie to the main quest, for many players, personal resolution to their goals can be just as meaningful.

Variant #1: The Party’s Journey: Players may need time to get into a roleplaying groove with one another. Creating space in which they can experiment with the group dynamics can be a valuable tool to facilitate this. Slower side quests, perhaps those involving travel or social encounters, can bridge this gap, especially for newer groups.

Variant #2: Player’s Choice: Some players will take initiative to suggest courses of action that are meaningful to their character but clearly not in the main plot’s structure. See if you can believably incorporate them, or provide the party the opportunity to pursue the idea. It will reward their attempts at collaboration.

C. The Amazing Idea
Oh boy, so you found the coolest space casino one-shot or funhouse dungeon! Or maybe you’ve been sitting on an idea for a villain for years, and you don’t know when you’ll get to GM another game. But you’re running from a published adventure, so your idea might not fit neatly into it.

Do it anyway. We could find exceptions to that advice, of course, but I’m a big believer that if a GM is passionate enough about an idea, they can nearly always make it work well.

D. Side Quest as Exploration
Have you ever had one of those nights (irl) where you don’t have a definite plan, but you just want to go out and do something. This might be accompanied by phrases like “we’ll see where the night takes us” or “we’re just kind of exploring.” These can be fun nights. Giving PCs the freedom to do the same can be equally interesting.

This is where random tables help. Scripting this sort of thing is likely to not work well. There are a handful of well-known old “carousing” tables that Gary Gygax put together, and he probably made them for when his players were going out for a night on the town after a hard dungeon dive. They wanted to see where the night took them. The trick, of course, is to take the 1-2 sentences from each entry on such tables, and build them out into a meaningful, though random, series of events. And while that focuses on city carousing, similar random events could be generated for any setting to satisfy a party’s wanderlust.

E. The Unknown
So imagine you’re running an adventure, and the plot is going along smoothly. And then…a massive, seemingly bottomless chasm opens up outside of town. Townsfolk talk about it, it attracts some interest. But nothing happens, and the players continue their quest(s).

Then…it expands. This time, it forms a perfect circle that’s too symmetrical to be natural. Yet, you still don’t explicitly tie it to the main quest. The allure of “what’s down the hole and why did it appear?” will be too much for many groups. Let their curiosity guide you to where your creative efforts should be focused.

IV. Size & Scope of Side Quests

I find it useful to categorize side quests into: Small, Medium and Large. The lines can of course blur between them, but they do have some descriptive value.

A. Small
These might simply be called “events” or “encounters” by some. But I prefer to think of them on the same spectrum. I generally group side quests into this bucket when they would be resolved in a single scene, or two at most. Many supplements have been created to this effect. They are more nuanced than simply a random encounter table, but small enough that they can be sprinkled throughout a campaign in any amount.

Example: One of the mice in the Mouse Guard, a grizzled veteran, has been assigned to guard a caravan as it travels to another city. Before he leaves, he is approached by a child and asked to tell a war story.

B. Medium
These are your classic one-shot insertions that take up most or all of a session. It generally requires some element of travel and multiple scenes using various skills.

Example: After the story, the mouse child reveals that his mother, who normally tells him stories, is very sick. Some investigation uncovers that the herbalists need the root of a rare plant to make the proper medicine for her. The root has been known to grow in a particular area that will take the caravan about a day off-course.

C. Large
This is what I’d start to call an “arc” of three or more sessions. This is often a character-specific arc, as detailed in section III, but can be for other reasons.

Example: The child’s mother turns out to be the wife of the PC’s fierce rival. Their hatred runs back to childhood. Her husband went to search for the root several days ago and has not returned. Despite their enmity, she asks the PC to search for her husband and see him safely returned if possible.

D. Incorporating Each
I think it’s important to vary these and include multiple side quests of each size, as well as various different types as listed in section III. Similarity begets stagnation, and variance is one of the easiest ways to maintain a flow to your campaigns while making the world seem dynamic.

There’s also a lot to be said for varying the rate at which you present these quests. “Hook density” is something that’s a bit beyond the purview of this article, but I’ve recorded my thoughts on it, and it touches on some of the same themes that are included here.