D&D Ideas — Side Quests (2024)

D&D Ideas — Side Quests

February 24, 2019

Adventure Hooks/ Character Stories/ / Game Master Tips/ Player tips/ YouTube

Welcome to another edition of the Nerdarchy Newsletter. This week we are talking about side quests in D&D. Our last weekly live chat was also on side quests in D&D. We figured there was more to be said on the subject.Let’s get into it.

D&D Ideas — Side Quests (1)

The ol’ Sumber Hills, rife with side quests and adventure from the fifth edition Dungeons & Dragons Princes of the Apocalypse. [Image courtesy Wizards of the Coast]

Delving Dave’s Dungeon

Side quests in D&D are a great tool for both players and Dungeon Masters alike. When the players pick the side quests I’d advise the Dungeon Master to pay attention. Or you can use it as a break from the ongoing plot. I won’t get deep into it because I think the other guys get into that deeper.

D&D ideas for side quests

  1. The Babe — Random encounter with ogres. They find more than treasure in its sack — a child. Do the players leave them alone in the wilderness? Do they escort them back to where they are from?
  2. Street Rat in the Market — A pickpocket makes off with a character’s pouch. Do the players leave it be or go after the thief?
  3. Mysterious Stranger on the Road — Kind of tropey but still fun. Do they have a curse, key, or information? Do they offer a reward for the retrieval of an item they need? Is someone after what the stranger has, or the stranger themselves? Maybe they’ve heard of the adventurers and sought them out for help intentionally whether the characters know it or not.
  4. It’s a Map, It’s a Map— A map as part of a treasure trove. Maybe it leads to a place of untold riches or power. There is a catch. The way only opens every 50, 100, 500, or however many years.
  5. Town Under Seige — Our adventurers are ready to leave town. Before they can marauders show up — orcs, goblins, gnolls, trolls, giants, bandits, or some other threat. Do the players sneak out of town? Do they stay and assist the town’s folk? Maybe they want something the characters have, making the adventurers partially responsible.
  6. A Friend in Need and Friend Indeed — An old friend, family member, or NPC they’ve dealt with in the past has a problem and wants the party’s help. Maybe someone is after them or has taken one of their loved ones. There should be a time limit. To make it a hard choice they either deal with the problem or there will be consequences for the NPCs.
  7. The Curse — One the characters picks up a curse during the game. Deal with the negatives or drop what you are doing to find a way to remove it.
  8. Where’d They Go — If you can’t make it to game night you might get kidnapped. I’ll often make a session around a player that can’t make it for a session. Especially if the adventuring party was in the middle of an adventure. The rest of the party will spend the session retrieving their missing companion. Or alternatively maybe they gotten sick or cursed and the rest of the party rushes off to find the cure.
  9. Mistaken Identity— The player characters are accused of something they didn’t do or they are thought to be someone else. They must clear their names or constantly be looking over their shoulders as outlaws.
  10. The Holiday Special –– I love running holiday-themed adventures for my players around the holidays. It’s just a fun diversion from the ongoing quest. This will vary depending the holiday. My personal favorite go to is to steal from kids’ holiday specials. Obviously the actual hook will vary depending on the holiday.
    1. Christmas— Someone has broken in and stolen all the toys from a northern village’s toy shop. It’s owned and run by gnomes.
    2. Halloween— Area is plagued by a headless horseman, ghost carriage, or scarecrows coming to life. Just pick your favorite horror movie.
    3. St. Patty’s Day — Cursed coin from a leprechaun’s pot of gold. Literally the plot from the Leprechaun movies.

Just some quick D&D ideas to throw into your game to get it off the beaten path and shake things up.

Out of Ted’s Head

Side quests are one of those things that pop up in games of all types. Board games and TTRPGs offer things that are not always related to the main quest and the hero or main characters have to decide — do they focus on the main plot or go see what this other thing leads to?

When they decide to go off the main path we have a side quest. Now sometimes characters want a side quest because they are bored with the main story. Another reason is the main story is too much and they need a breather. This might be a way to break up a heavy mental or gory game and add in some jovial fun.

For me the main reason to offer a side quest is to actually give a player character a chance to progress their story. This works well when the player and DM are in communication and are able to work together on the character goals. These side quests have the ability to take part in small chunks over time. They need not draw out the whole party and force them on an adventure. I’m not saying you can’t do this but a side quest need not need the whole party when it is just a simple conversation and can lead to further adventure later.

Lastly let me throw this out there. Side quests can be a lot of fun and can be a cool deviation from everything you are doing. It can even impact the story or the main plot even if the characters were not expecting it to. But since a side quest might not always get a bite or interest from the party, how do you manage? This is quite simple. Just like throwing bird seed out to feed the birds you have to throw out a lot of hooks. You could describe a woman who was captured in a multitude of ways:

  • A random citizen talks of a missing girl and people have gone looking for her, but to no avail
  • The tavern owner is distracted when serving the adventurers and informs them of his kidnapped daughter
  • People saw goblins sneaking around town last night.

There is no immediate connection behind these random descriptions but they are all clues on the same event. If you know your players and the kind of hooks they might follow then it is no big deal, but of you are never sure you have baited the hook in a multitude of ways to see what they might go after. Now you can use the idea of throwing out lots of hooks that lead to different side quests, lots of hooks that lead to the same quest and you can use this strategy for your main quest or the side quest.

From the Nerditor’s Desk

When is a side quest a main quest?

Thinking about side quests in D&D is kind of a tough topic for me. Most of the games I run, and many of the ones I enjoy playing in the most, have no main quest so the idea of quests tangential to a primary plot is not in my wheelhouse. The main quest, in the majority of cases, is adventuring as a vocation.

As a Dungeon Master I am a big fan of letting the players guide the direction of a campaign. My role is to help them tell the story of their characters. Along the journey, they pursue their goals, explore, grow in power and so forth, and between their speculations and my collection of tweaked and tailored adventure modules a story emerges. All of those little quests along the way combine into the tale of the adventuring party.

As a function of the game, a quest offers a challenging journey towards a specific goal. In the campaign we recently started, the characters are just barely 2nd level and they’ve completed several quests like the Quest to Introduce Themselves in the faraway village they were sent to and the Quest to Find a Place to Live. I am not joking — those activities presented unique and engaging challenges for the characters and they were rewarded for completing them.

(They also granted peace to a troubled specter in the Quest to Explore the Ruined Lighthouse.)

Over the course of two game sessions where the party never left town, they kept themselves plenty busy roleplaying with the NPC residents and filling out their own quest log of things they want to look into. A missing person, a local tall tale, an ancient artifact, and a ship of despicable marauders are all quests that emerged purely through the players walking around town getting to know their new neighbors. None of these are quests I had in mind to seed the campaign with, I just listened to the players and adapted to what they excitedly talked to each other about.

They’re also convinced some ominous event occurred 8 months prior to their arrival. Spoilers for players in my game: it was just a throwaway amount of time I happened to tell them for two different events. But hey, sounds cool to me and there’s another quest for them to pursue: the Quest to Find Out What Happened 8 Months Ago.

This kind of campaign isn’t for everyone, of course, and your mileage may vary with letting the players discover and uncover their own quest. Player-generated side quests can be tricky if the adventuring party is on a Big Damn Quest and time is a factor. But there’s a way for a DM to incorporate player side quests in these scenarios too.

If you take one element of your epic adventure and think about how it might fit into a side quest the players really want to undertake, you can still move the larger story forward and satisfy the players at the same time.

For my money, Chris Perkins is a master at this kind of free-flowing adventure. He does a wonderful job for players in his game of sharing the driver’s seat, encouraging them to paint the scenes and embellish with their own tastes and imagination. This is especially evident in Dice, Camera, Action because the campaign arcs are based on official D&D adventure stories, but they ebb and flow. The interactions between Chris and the Waffle Crew illustrate perfectly how people can take published adventures and make them their own. The diversions created by the group manifest in their own side quests, and the tapestry of their story is all the better for it.

Side quests: use them! If you’re a player, listen to your character — as they develop during a campaign they’ll inform you of side quests that’ll enrich the experience. If you’re a DM, listen to your players and encourage their ideas. Between sessions, consider how their speculations and ambitions can become side quests that make the story of their characters a special one your group will never forget.

As a bonus, our friends at Limitless Adventures publishes a series of web posts every Friday with 20 one-sentence quest ideas for specific classes and races. They invited me to contribute, and I shared 20 side quest ideas for rangers. If you are interested, check it out here and let me know what you think in the comments below.

Until next time “Stay Nerdy”

Nerdarchy Team

P.S. In case you missed this recent video from channel

5E D&D Feats – A Cleric’s Guide

D&D Ideas — Side Quests (2024)


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