Creating a Halfling Rogue DnD 5e: The Iconic Stealthy Burglar

Last Updated on January 22, 2023

The halfling rogue (or thief if you’re old school) is one of D&D’s truly quintessential pairings. It’s the dextrous peanut butter and razorblade-laced chocolate of the hobby.

Maybe it’s more or less iconic than the elven ranger or the dwarven cleric, but there’s a reason why the pregenerated rogue in the D&D Starter Set is a lightfoot halfling: it’s an indisputable classic. 

So, if you want to play one of the truly timeless race-class combos in D&D 5e, this is our comprehensive guide to building the ultimate halfling rogue. 

Creating a Halfling Rogue 

Let’s look at some of the benefits of using a halfling as the basis for your next rogue, from their ability scores to racial traits, as well as which backgrounds and starting gear to choose when looking to embody the quintessential thief. 

Ability Scores 

A rogue’s first and foremost concern when assigning ability scores should always be Dexterity.

This stat defines your weapon attacks, contributes to your Armor Class, your initiative rolls (absolutely essential if you decide to favor stabbing over sneaking and stealing stuff), and is the driving force behind some of the most roguish skills (sleight of hand, acrobatics, and stealth). After that, it kind of depends on what kind of rogue you want to play. 

Rogues were among the earliest classes introduced to D&D all the way back in November of 1979 as part of the game’s very first supplement: Greyhawk. Back in the early days, rogues drew a great deal of inspiration from a particular halfling, whose guile and talent for burglary are definitely the stuff of legends. 

As a result, the thief class (as it was called back then) was far more geared towards exploration, disarming traps, and emptying the bad guys’ treasure vault while the rest of the party did the actual fighting. 

Over the years and editions, rogues have – I think – found themselves increasingly geared towards combat, with things like Sneak Attack becoming their defining ability and their proficiency with Thieves’ Tools, and their ability to pickpocket enemies or evade detection fading to the point of being kind of an afterthought.

This trend peaked in 4e (admittedly a much more combat-focused version of D&D in general) and in the current rendition of the game, it’s started to swing back the other way through several subclasses that push the rogue towards a healthier blend between sneaking and stabbing. More on this in a minute. 

Whether you want your halfling rogue to emphasize the sneakier or, er, stabbier components of a rogue can influence where you put secondary emphasis in your ability scores.

If you want to be a charming scoundrel with a talent for smooth-talking your way past dragons and city guards alike, buff your Charisma; if you want to devote yourself wholly to striking down your enemies, then maybe Constitution is the way to go.

There are arguments to be made for Intelligence and Wisdom as well. There is no argument to be made for Strength. Just leave it alone. 

A halfling’s natural ability score bonuses make them ideally suited to just about any sort of rogue you have a hankering to play. All halflings get a +2 bonus to their Dexterity, which helps get your highest stat as high as it can go.

And then, depending on which subrace you choose to play, you can emphasize one of the two best secondary ability scores for a rogue. 

The Lightfoot Halfling increases their Charisma by +1, and the Stout Halfling can increase their Constitution by +1.  

Halfling Racial Traits

In addition to a juicy +2 Dexterity bonus, all halflings have the following traits. 

As if that weren’t good enough, each halfling subrace also gives you a little something – both of which are thematically and mechanically great for a rogue. 

Lightfoot Halfling

As well as a nice +1 to your Charisma, the lightfoot halfling excels at staying out of sight.

Your Naturally Stealthy ability means you can attempt to take the hide action even when you are obscured only by a creature that is at least one size larger than you. If the idea of ducking out of view behind the party’s tank doesn’t scream “rogue” to you, I don’t know what will. 

If you want to play the sneak thief rogue who moves unseen through the shadows to make off with the villain’s shiniest loot, play a lightfoot halfling. 

Stout Halfling

As The Lord of the Rings informed us many times, the halflings are highly resilient creatures – whether they’re resisting the effects of the One Ring or just a big ol’ rip of longbottom leaf – and the Stout halfling embodies that to a tee.

You not only get the +1 Constitution bonus, but you also gain advantage on saving throws against poison, and you have resistance against poison damage. Perfect for a machiavellian poisoner or assassin. 

If you want to focus on the rogue’s role as a nimble, lethal damage dealer, play a Stout halfling. 

Skills

All rogues make for excellent “skill monkeys” – characters that can do a lot of stuff and do it well. While halflings don’t get any skills as a result of their race, there are plenty of skills that synergize well with their ability score bonuses to help you be the best rogue you can be. 

Also, your roguish Expertise allows you to double up your proficiency bonus on a number of the skills you want to be best at. 

All rogues choose four options from the following list of skills at character creation: Acrobatics, Athletics, Deception, Insight, Intimidation, Investigation, Perception, Performance, Persuasion, Sleight of Hand, and Stealth

Backgrounds

In addition to a wealth of useful skills, languages, proficiencies, and equipment, each Background gives you a little extra narrative ability, not to mention helps flesh out your backstory. 

If you’re playing a halfling rogue, try picking one of these backgrounds:

Charlatan

You’re a confidence trickster, a hustler, a lovable scamp with a heart of gold. Charlatans excel at getting what they want out of people.

You gain proficiency in Deception and Sleight of Hand (leaving you free to grab some other skills from the base rogue’s extensive list), as well as proficiency with a Disguise Kit and a Forgery Kit.

For equipment, you get fine clothes, a disguise kit of your own (you’ll have to find a forgery kit later), 15gp, and one of the best and most open-ended starting items: “tools of the con of your choice (ten stoppered bottles filled with colored liquid, a set of weighted dice, a deck of marked cards, or a signet ring of an imaginary duke).”

Also, you gain the special feature False Identity, which gives you a second persona, including the necessary forged documents, established acquaintances, and disguises that allow you to assume it. All around awesome and archetypically roguish.

Criminal

Take a slightly longer detour into crime with the Criminal/Spy background, which gives you Deception and Stealth proficiency, as proficiency with a gaming set, a useful pile of equipment that includes a crowbar (most underrated gear in the game), and a network of contacts throughout the local criminal underworld. 

Urchin

If you’re playing in a more urban campaign, the Urchin provides Sleight of Hand and Stealth proficiency, as well as disguise kit proficiency, and a working knowledge of the hidden secrets, rhythms, and flow of your home city. 

Starting Gear 

Depending on your choice of background, you could easily start your halfling rogue out with a disguise and/or forgery kit. 

Playing a rogue gives you proficiency in Simple weapons, hand crossbows, longswords, rapiers, shortswords, Light Armor, and Thieves’ tools.

When you create your character, you’ll also get access to the following: 

• (a) a rapier or (b) a shortsword
• (a) a shortbow and quiver of 20 arrows or (b) a shortsword
• (a) a burglar’s pack, (b) a dungeoneer’s pack, or (c) an explorer’s pack
• Leather armor, two daggers, and thieves’ tools

For a sneaky rogue, grab a rapier and a shortbow, as well as a burglar’s pack. For a stabby rogue, grab two shortswords and a dungeoneer’s pack. 

Subclasses, Feats, and using your abilities 

Whether you want to take your halfling rogue down the path of sneaking or stabbing, you’ll cement that decision at 3rd level when it comes time to choose your Roguish Archetype. Then, I’ve lined up a few feats that suit the halfling rogue.

Subclasses: Sneaking and/or Stabbing 

There are plenty of other types of rogue you can play, from a cunning political mastermind to a respectable magic user. However, these are all noticeable diversions from the two classic archetypes the halfling rogue embodies (and there are other races better suited to playing them.

For now, let’s look at two contrasting options for a Roguish Archetype you can choose at 3rd level. 

The Assassin

If it’s stabbing you want to emphasize – the ability to leap unseen from the darkness and bury a blade in your enemy’s throat – then the Assassin is the subclass for you. You gain extra damage and advantage on attacks against people who act after you in the initiative order.

You also get some useful infiltration and disguise abilities that can be invaluable in ensuring that your target doesn’t see you coming until there’s a dagger in their back. 

You can check out our in-depth guide to the Assassin subclass here. 

The Thief

if you want to lean into the rogue’s heritage and flair for dungeon delving, trickery, and generally being a sneaky little weasel (looking at you, Bilbo), then the Thief subclass is for you.

You become increasingly dextrous with your sleight of hand abilities, even in the midst of combat; you can climb, jump, and sneak better than just about anyone else; and (in reference to an ability native to thieves in 1979 Greyhawk supplement) you can even figure out how to improvise the use of items even when they are not intended for you. 

Feats

Alert: Perfect for the Assassin subclass, this feat gives you a +5 bonus to your initiative rolls, ensuring that your enemies need to get up pretty early in the morning to get the better of you. 

Lucky: want to double down on the halfling’s ability to reroll natural 1s? Grab the Lucky feat to reroll three skill checks, saving throws, or attack rolls per day. 

Poisoner: this Feat lets you craft poisons in an hour, as opposed to over an extended period of downtime that it takes everyone else. If you’re playing a Stout halfling, the resistance to poison damage is also going to come in handy in case of a failed roll or two. 

Tips & Tricks: Using Sneak Attack, Uncanny Dodge, and Other Classic Roguish Abilities

Regardless of the kind of halfling rogue you want to play, there are few tips and tricks that help you make the most of your roguish and halfling abilities. 

Don’t Go First

Your halfling ability to move through a larger creature’s space, as well as the lightfoot halfling’s ability to hide behind another creature, means that you should pretty much always be lurking in someone’s shadow. 

Prioritize your Sneak Attack

Sneak Attack is your best source of damage as you level up since the rogue doesn’t get extra attacks like the fighter or paladin. If you have advantage on your attack roll (when attacking from hidden, for example) or if an ally is within 5ft of your target, you get to add one or more d6 to your damage roll.

Whether you’re playing a sneaky burglar or a stabby assassin, engineering situations in which you can apply your Sneak Attack damage is critical to playing any kind of rogue.

As a halfling, your small size and ability to conceal yourself behind your allies is a huge part of this. 

Choose the Right Expertise

Rogues are already good at a lot of things, but Expertise makes them even better. Starting at 1st level, you get to pick two skills (I would prioritize Stealth for more effectively hiding in order to gain advantage and therefore more reliable Sneak Attack damage) and double your proficiency bonus when making checks using those skills.

Later on, your proficiency bonus goes up and you can apply your Expertise to more skills. Pick the ones that suit the type of halfling rogue you’re playing. If you’re a charlatan, a fraudster, and an all-around social weasel, put Expertise into Deception or Persuasion.

If you’re a burglar who’s all about passing unseen, choose Acrobatics and Stealth. And so on… 

Use Your Cunning Action Whenever Possible

Cunning Action is, in my opinion, the strongest rogue ability in the game, and synergizes really well with the halfling’s natural sneakiness. Cunning Action allows you to use your bonus action to take the Dash, Disengage, or Hide action.

Dashing compensates for the halfling’s mediocre speed; Disengage lets you get back behind your party’s tank after dealing some nasty sneak attack damage, and Hide lets you melt back into the shadows to get advantage on your next hit.