BoLS logo Tabletop, RPGs & Pop Culture

D&D: 13 Sidequests That Will Make Any Background Shine

6 Minute Read
Jul 20 2021

Backgrounds are one of the most underrated parts of the Player’s Handbook. Let’s fix that with these 13 different sidequests. One for each background.

It’s no secret that one of the best ways to give characters something interesting to do in a game is to draw on their backstory. If your player has come to you with 16 pages of NPCs, story, and history, odds are good they’re hoping some of it gets used. And if they haven’t, well, count your lucky stars. But they’re still probably hoping for a time in the spotlight. But even if they haven’t written a single thing, there’s still one thing you can use to give any character a story: their background.

Yes, backgrounds of all shapes and sizes are a fantastic way to hang character specifics out for a day in the sun at your tabletop. Got a Fighter looking for something to do? Bard bored and brooding? Just use one of these background subquests and you’ll have them engaged in an entertaining B or C plot in no time. We’ve got one for each background, so strap in.


Acolytes can perform the religious ceremonies of their deities. Why not turn that can-do in to a to-do. As part of this sidequest, characters with the Acolyte background are called on to perform a religious ceremony:

Ceremony Type (d8):

  1. Wedding
  2. Coming of Age
  3. Funera
  4. Feast Da
  5. Settle a theological disput
  6. Settle a local disput
  7. Bestowing a Blessing on someone/somethin
  8. Esoteric mystic/gnostic rite


Figure out some components or symbolic gestures or acts they’ll need to do, and set them on the road of actually being an acolyte of their deity.


Charlatans are con artists, scammers, and thieves. Their knack for stretching the truth can get them into and out of trouble as often as not. One thing all Charlatans have in common though is a False Identity that lets them forge documents and official papers. But sometimes the False Identity might have a life of its own.


When entering a town, the Charlatan is immediately recognized by someone as their False Identity persona, and whoever recognizes them will not hear otherwise. They need the Charlatan’s help in dealing with another Official (or persona of the appropriate type), and call upon them to come argue in their favor.


Criminals are all about crimes–and their feature gives them access to a network of other criminals whom they can call on for aid in dire times. But contacts are a two-way street.

When coming downstairs for breakfast, the Criminal is greeted by their contact, who may or may not be in disguise. They are in need of help:

You Gotta Help Me (d4):

  1. Lying low and hiding out from the authorities/rival criminals
  2. Pulling off a tricky job
  3. Fencing an item
  4. Doing some ‘honest’ work for a while


Entertainers are consummate performers. Whether they are jugglers, actors, jesters, storytellers, or mimes, Entertainers can always find a place to perform. But sometimes the place finds them–recognized by a local official, the Performer is formally requested to be in charge of a local festival. They must find at least three other ‘acts’ in order to put the festival together.

Folk Hero

Folk Heroes are people who have come from humble beginnings to go on to do great thing. They are heroes plucked up from among the common people, and can always find a place to hide, rest, or recuperate among them. In fact, people who recognize the character might call on them to give a speech.

The Folk Hero is given a quest to deliver a rousing speech. Or break new ground for a temple/merchant consortium/guild hall. Their rustic fame will surely bring out the crowds.


Guild Artisan

Guild Artisans are tradespeople and crafters and artisans. In addition to having proficiency with some trade skill, the Guild Artisan has access to the guildhalls, favors, and friends of the Guild they belong to.

However they are expected to pay dues–and let’s go a step further and have them attend a Guild Meeting where they’re given a task to complete to help further the Guild’s interests in a town. This could be securing a trade deal, gaining ownership of a building, or some other task like that.


Hermits isolate themselves from the world but learn a secret truth about the nature of the world. They have had a powerful revelation made to them, making this one of my favorite backgrounds, because it practically generates its own quest right then and there.

But you can go a different route and not tie a Hermit sidequest to the big revelation. Instead, a petitioner–someone who has heard of the hermit’s wisdom or revelation, comes to the Hermit seeking guidance with a problem. Guidance that relies on some facet of their big secret.


Nobles have wealth, power, and privilege. They are members of a noble family, and are welcome in high society and places where high society is respected. Nobles might be able to speak to other nobles–but this also comes with duties. The Noble is called upon to oversee noble activities, as is their familial duty.

Noble Duty (d6):

  1. Judging a tournament
  2. Competing in a tournament
  3. Attending a landholders meeting and casting a vote
  4. Hosting a lavish ball
  5. Being present at Court for an important matter
  6. Holding a feast for peasants and nobles alike


Outlanders grew up in the wild places of the world. They have an excellent memory for maps and geography and can make sure their party is well fed and supplied when wandering in the wilderness.


But sometimes that natural world is in need of protection. The Outlander learns of a camp of laborers who would be cutting down a sacred grove or other territory the Outlander loves. The Outlander is called on to find a solution (preferably a peaceful one).


Sages are scholars and academics. They study the lore of the multiverse and are so well versed in their own research that they know where to find information that they cannot themselves recover.

However, when a rival Sage comes to town and loudly denounces the Sage’s theories, it’s time for a no-holds-barred academic symposium, with the Sage being called on to answer this impostor’s spurious knowledge.


Sailors, as the name implies, are great at sailing. They might have their own ship, or have worked on a ship for a while. When pressed, they can secure free passage on a sailing ship for themselves and their party. But sometimes being a great Sailor means being the only one who can navigate things.

The Sailor is called on to either help crew a ship or steer a ship through a narrow inlet or river or the like. They aren’t just there to make Sailing checks, but rather to help a bunch of non-boaters survive their harrowing crossing.


Soldiers were once members of a standing army or mercenary company or maybe even just a local militia. Whatever their army, they can still enjoy the benefits of their Military Rank. But while rank hath its privileges, it is not without its responsibilities.

The Soldier comes across another member of their former unit/outfit/company, who is in dire need of help:

I Need Your Help (d6)

  1. Healing
  2. Shelter
  3. Assistance paying off a debt
  4. A family member rescued
  5. Getting in to plead their case before the local authorities
  6. They’ve been condemned for a crime they didn’t commit!


Urchins are your orphans and street dweller types. They grew up on the meanest streets of a city and had to provide for themselves. Not only did they survive, but they thrived. And in game terms, they know the secrets and passages through an Urban area.


Someone claims to know something about the Urchin’s real parents, whom they never met. The Urchin must try and track down this mysterious person and discover what, if anything, they know…

There you have it folks. A fine bunch of Sidequests for any Background. Enjoy!

And as always, Happy Adventuring!

  • D&D Live Told Us More About The Next Three Very Different 5E Books