D&D Has Consumed Me -- Now I Want to Try DMing :)

Hi everyone! :))
I’m looking for recommendations for a fun, beginner-friendly one-shot or short adventure for a first-time DM (me) and probably 3-5 players, most would be completely new. We’d be playing in person.

I’m pretty new to D&D myself and only partway through my first campaign, but I already love it and want to play more. I watch a lot of Critical Role and Dimension 20 now.. it's kind of consumed me.. in the best way! I even designed, printed, and painted custom minis for myself and the other players in my current campaign - so I may be new, but I’m already deep in it haha

I have purchased and started working through the DMG and the Monster Manual is on the way. 

I'm really most familiar with the revised 2024/5.5e rules. I’ve also used some material from Tasha’s and Xanathar’s, although I’m thinking I should keep things primarily to the 2024 rules, maybe that would be easier for a table of new players (and new DM lol).

I’d love something with more of a funny, classic-fantasy feel (basically doesn’t have to specifically be any type of setting or whatever) with a mix of roleplay, exploration, and combat. But most importantly, it would be fairly easy for a new DM to prepare and could be completed in one longer session or a few shorter sessions.

One important note: I’m currently playing through a homebrewed version of Lost Mine of Phandelver, so please don’t recommend that one - or share any spoilers please! I’ve intentionally avoided reading the published adventure or anything else about it.

I’m also curious about character creation for first-time players. Is it better to use premade characters, help everyone make their own, or offer both? I was thinking level 1 or 2, but I’m open to suggestions if another level works better for a first game.

I’d also appreciate recommendations for where to find good one-shots, whether that’s through D&D Beyond, an official book, or a third-party creator.

Finally, if this goes well, I’d eventually love to create my own adventures or campaign setting. What do you use to organize your worldbuilding, NPCs, locations, session notes, maps, and everything else? Are the tools on D&D Beyond enough, or would you recommend something like Kanka, World Anvil, Notion, Obsidian etc? A combination?

Basically, I would love any recommendations for:

• Beginner-friendly one-shots or short adventures
• Premade versus player-created characters
• The best starting level for completely new players
• First-time DM advice
• Worldbuilding and campaign-organization tools

Thanksssss :) 

Honestly, the only real starting adventure for 5.5e is Heroes of the Borderlands. Beyond that 5.5e's adventures are somewhat underwhelming in my opinion. Kobold Press did recently launch a version of their Northlands setting with some one-shots and adventures, and those folks know how to write fun adventures. They've got versions for both their own system Tales of the Valiant, and 5.5e.

If you're willing to overlook that it will be a lot easier for player characters, I'd suggest Dragon of Icespire Peak. It's built for 5e (and yes that does make a difference), but it's a good fun 'quest board' style adventure. The module was built in my opinion more for DMs than players in that it really does model how to give short descriptions of the areas and environments, it draws the NPCs a little better than in LMoPhandelver. If you're set on 5.5e though, I'd suggest swapping the monster stat blocks from Icespire Peak with the ones found in the 5.5e Monster Manual.

Icespire Peak is a great campaign so I’d second Martin on that one. However it is a full campaign so if you’re just looking for one shots I highly recommend Wild Sheep Chase or Wolves of Wheldon, both free and easily available with a quick google. They’re fairly light hearted little adventures, one trying to help a wizard that’s been turned into a sheep, the other investigating some wolves that seem to be kidnapping sheep rather than eating them, and both offer a good variety of combat and social encounters. If you’re looking fir a full collection of one shots imo the best official anthologies are Candlekeep Mysteries and Journeys Through The Radiant Citadel but for sheer numbers it’s hard to beat One Shot Wonders, a third party book with a hundred one shots all formatted to two pages so they’re easy to run with a minimum of prep time.

As for creating characters v Pregen it’s something you’d need to ask the players. Character creation can be really boring the first time you do it, it takes a long time and if you don’t know what you’re doing theres lots of decisions you don’t understand and a lot of options to confuse you. On the other hand lots of people get less invested in Pregens because it’s not their character. The third option is D&D Beyonds quick build, you choose a species, a class and a background and then it builds a character. It’s pretty good and you end up with a balance of speed to create but still feeling like the character is unique and you. The characters are level 1 which means you’re very squish with few hit points but is I think the best place to start new players. They’ve got enough on their plates learning which die is which and what to roll and add on without having lots of options from starting at higher levels.

For organisation I’m old fashioned and just have a note book and a tablet full of setting pdfs I can notate, but I know lots of people swear by things like World Anvil or Obsidian although I’ve never got on with either. They’ve got free trials so might be worth trying to see what you like, there’s also plenty of YouTube videos explaining them. I know a channel called Mystic Arts has a full two hour video on how to use Obsidian and why he likes it (he’s also worth a follow as a new DM as he’s great for how to videos and tips)

Notebooks. Take notes on what happens during the game so you can recall it later.

Make lists of names and places so when a player asks, what is this guys name? You look at your list and have it.

Ask the players what kind of character they want to create - give them examples from movies or pop culture, let them know they are just starting so will be kind of weak.

I would start with Standard Algorithm rather than rolling because rolling for stats can feel shitty for a first time player if they roll bad. Standard allows you the opportunity to explain to the party that they should consider putting the 15 in a place that makes sense for their class.

If you don't know a specific rule, it's ok to tell the party this and go with the flow instead of stopping the game. You tell them you will look it up later but for now, it works how you call it.

Small warning: You're probably going to end up making an NPC you had not meant to make. I certainly have quite a bit, so know that if you make a joke character to just use as the bartender of a merchant and your players like them, it's somewhat likely they'll try to recruit them somehow. This has happened at least twice with me,. The first guy was named Tyler and the second was, ironically, named Swim Shady. He's a triton.

The Wild Sheep Chase is a great one to start with. The only caveat is that it's set at level 4-5 which means there is a bit more to learn. With new players and a new DM I'd probably set them up at level 4 (basically level 3 and then have them choose ASIs rather than feats). I've seen people run it at lower levels but I haven't seen how they adjust the encounters. It is nice that at this level you get quite interesting enemies. It's funny, it's relatable, and you can find a fully prepped version of it with all the maps, so it's pretty much ready to go.

Pregen vs letting your players make characters: I think that's about what your players are like. If they are crunchy and like to get into it, I think making characters themselves is always better - you at least have some idea of choices you made. But pregen is a thing too. Don't get caught up in "optimal mixes" of a party. You can work with whatever combination they make. And if they don't have a healer, you can stash some potions or a useful NPC in the environment.

Your players might appreciate the character builder here on DNDBeyond even if you'll play in person. It's free for the SRD classes. It walks them through the choices which is helpful. Then, you can print the sheet as a PDF to play with paper.

I'd definitely pick something short for a first game that comes to some sort of conclusion. Then at the end there's a decision point, do we like this, should we play more? My players were RPing and chatting a lot, so I think we ran two three hour sessions. You can probably do the Sheep Chase in 4 hours if there's less of that.

I end up just using google docs for my organization and notes. I've also tried Obsidian. I don't find that I need that much structure for a one-shot, though there's a lot to like about it. If you're making a more complex world and plot Obsidian starts to be really interesting.

For starting levels: Level 1 is of course the tutorial level. Not so many choices, and the characters are quite squishy. I think there's value in starting here if you have players with a strong attention span. They'll get good fundamentals. 

If you think they want something more splashy, level 3 is also a good place to start and learn. They have a bit more resilience and it's okay if they don't use all their features.

I agree, this is a great starting oneshot.

A few:

• Dragon of Icespire Peak
• Dragons of Stormwreck Isle
• Heroes of the Borderlands

These three are official and built for starting out as a DM and a player. You have vetoed Phandelver, which is my favorite of the batch of starter kits. It's what I learned on, and I recommend it to basically everyone.

Players will have much more fun with characters they make. Having a piece of paper with a whole bunch of numbers on it being set in front of you is way less engaging and personalized than a blank piece of paper you get to write the numbers on.

Start at level one. Starting at higher levels make things much more complicated, and for a first time, unnecessarily so.

I use Docs to track my stuff. Nothing fancy, just paragraphs and bullet points for my campaign, split over several tabs, and for my world, a lot of different tabs and a mess of half organized and half completed blocks of words that nobody will ever read. You don't really even need that much to organize. Simple lists work fine for me.

Dragon of Icespire Peak is a great start, Phandelver is my personal favorite but Icespire Peak is a good second. If you want just a one-shot and not an adventure, Secrets of Sokol Keep is an Adventurer's League module for levels 1-4 that is really easy to run, and can be done in a single session. I ran it for my sister/her friends who'd never played before and they had a great time. You can find it on DMsGuild for like $3. 

Start at level 1, it's way easier to figure out the mechanics/dice rolling/etc without the extra abilities that come with higher levels. Set the expectation that level 1 characters won't feel very exciting, but it's the best way to learn to play.

Let them make their own characters. I find that new players start to pick up on the lingo/mechanics as they go through character creation, which can make actual gameplay smoother. Plus they'll have way more fun with something they created, instead of just a sheet full of numbers they don't really understand. The dndbeyond character sheets are really helpful when making characters as new players, it walks you through it and the SRD classes/rules are free. Sticking with SRD classes reduces options, which can make it seem much less overwhelming. 

I just use Word docs for campaign building. I have a bunch of folders to keep things organized - one for character backstories, one for my world building/campaign story stuff, one for my weekly campaign recaps that I send after every session (my players are notoriously bad note takers, and after 10 years of playing with this group I've learned it's easier for my sanity if I send a recap right after the session.), and then I have a folder for each "chapter" of the story...breakdowns of locations w/ bullet points for shops/taverns/NPCs, dungeons with my bullet points for room descriptions, etc. Nothing fancy, basically just lists I can pull up when my players go somewhere. I run home-brew stories set in Forgotten Realms, so if they go somewhere unexpected I just use Google mid-session and/or make stuff up. I keep a blank Word doc open during gameplay so I can make quick notes of the things I make up/improv so I can add it to my notes later. I like Excel to track NPCs/open quests, kinda like a video game quest journal. It's very chaotic if anyone else looks at it but it works for me lol. 

If I'm running a one shot, I just use a single Word doc with bullet points and any read-aloud text so I'm not trying to read through the entire module mid-session. I'll read through it and do my prep notes like a day before usually.