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.