Category: Playing D&D

Custom Backgrounds, classes, advice and more about Dungeons & Dragons

  • Cabbies and ferien – people moving backgrounds for 5e/5.5 D&D and Black Flag

    Cabbies and ferien – people moving backgrounds for 5e/5.5 D&D and Black Flag

    Paths and ways in a fantasy world are not just occupied with masses of people walking with a few nobles on horseback. They are also clogged with carriages and carts delivering goods. In my own world one NPC used two giant turkeys to pull his coffee delivery cart. The players enjoyed the presence of this NPC so much they kept bringing him back up.

    The cabbie or ferien are taxis for a world where there are dragons and very expensive teleport circles.

    Cabbie

    You help carry people and goods between neighborhoods and distances. Working in urban areas either on the land or water you know the paths between places and the peoples who inhabit them.

    The cabbie may pull their own cart, use a pony or even have experience with a two-horse carriage. Often they have a stool to help their clientele into their car. Also willing to talk, even when the occupant isn’t interested, the cabbie can learn the happenings of a region or distract that occupant in such a way that they are susceptible to crimes.

    Cabbie (5e / 2014)

    Skill Proficiencies: Insight, Deception or Persuasion
    Tool Proficiencies: Vehicles (pick one of land or water)
    Languages: One additional language, often from a culture that is nearby the home of the character
    Equipment: Cart, carriage, rowboat, gondola, sailboat (pick one), a lantern with 3 flasks of oil, traveler’s clothes, a trinket, 2 days rations, pouch with 25 silver

    Feature: Talk too much

    You are a skilled conversationalist that frequently goes on and on. These long talks are often consuming and distracting. Some cabbies and feriens may have allies who use that speech as a distraction to pick pockets or similar events.

    Additionally, you pick up the streets, rivers or flyways of a new city quickly almost never getting lost in natural urban areas.

    Personality

    Use the Folk Hero and Fisher for guidance.

    Alternate: Ferien

    First, let’s get this out of the way. There’s no simple gender neutral word for ferryman. Similar to Anagod on World Anvil, I appreciate the older English word ferien. As you expect the cabbie knows the streets of a city or the ways between villages, the ferien works the waterways of a land — rivers, canals, lakes and shores.

    Image from page 270 of Medieval and modern times; an introduction to the history of western Europe form the dissolution of the Roman empire to the present time (1919)
    A scene in Venice – public domain

    It’s pretty simple to make the Ferien version. Choose Vehicles (water) and then pick a rowboat, canoe, gondola or tiny sailboat for the vehicle. Nothing else needs to change.

    Cabbie (5.5e / 2024)

    Ability scores: Charisma, Strength, Wisdom
    Feat: Talk Too Much
    Skill Proficiencies: Insight, Deception or Persuasion
    Tool Proficiency: Navigator’s Tools (2024 depreciated Vehicles)
    Equipment: Cart, carriage, rowboat, gondola, sailboat (pick one), a lantern with 3 flasks of oil, traveler’s clothes, a trinket, 2 days rations, pouch with 25 silver or 20 gold.

    Origin Feat: Talk Too Much

    Shoulder talking. When talking to creature with which you share a language (or culture) you are able to distract a non-hostile creature. An ally attempting use Sleight of Hand, Stealth, or Deception against that creature has advantage in the current minute.

    Paths and landmarks. After spending an hour in a bar, market, restaurant or other third place in a new non-magical urban area you are unable to get lost.

    Cabbie (Black Flag)

    Skill Proficiencies: Insight, Deception or Persuasion
    Additional Proficiencies: Vehicle (land, water to be a ferrien)
    Equipment: Cart, carriage, rowboat, gondola, sailboat (pick one), a lantern with 3 flasks of oil, traveler’s clothes, a trinket, 2 days rations, pouch with 25 silver or 20 gold.

    Talent

    You are familiar with the conversations and flow of urban places, used to finding your way through new cities and old while talking to people across social class, faiths or ancestries. Pick one of the following;

    1. Polyglot
    2. Trade Skills
    3. Aware

    Design Goals

    Watching Shadow & Bone, or the Lion, the Witch and the Wardrobe, you see that those who manage transportation are part of fantasy stories. Whether the carriage driver or the polemaster in a gondola, these characters deserve the opportunity to be heroes.

    Maybe because I’ve been focused on the bog-city of Sheljar for Dungeon 23 I thought it was time to share this background publicly. The bog-city, or an island city, must have peoples who are dedicated to navigating the waters.

    This post was originally written for 5e in January 2023 and updated for 5.5e and Black Flag in July 2026.

    Custom Backgrounds for 5th edition Dungeons & Dragons

  • ‘Wine lets secrets out’ – the Vintner, a 5e, 5.5e and Black Flag D&D Background

    ‘Wine lets secrets out’ – the Vintner, a 5e, 5.5e and Black Flag D&D Background

    On a family vineyard with vines as thick as hippogriff legs you work the grapes. The slow, tedious springs and summers on the hard scrabble rocks are exhausting, the harvest a frenzy of activity. Then the fun starts, as does the waiting.

    The vintner enjoys all of this time, but the apex of their art is the finished bottle, and sharing it with others. They carry stories in their bottles. Stories of grapes, of skies full of wyvern, of the journey past the bandit camps, of that one time the mage saved their vines, and that other time when the druid thought they were helping.

    Every bottle has a story as does every person who sips it. The vintner is not just an expert at crafting wines. They are a marketing specialist and a storyteller. Each barrel, every cork, each wineskin, every jug – another tale to tell is discovered. The vintner may not have intended to travel the lands on quests, but they know whenever they return to their villa and vineyard they’ll have new discoveries to share.

    Vintner (2014/5e)

    Skill Proficiencies: Nature and one of Deception or Persuasion
    Tool Proficiencies: Farming Tools, Winemaking Tools
    Languages: None
    Equipment: Farming Tools, common clothes, 1 pound of cheese, 3 wine skins, 3 small cups or glasses, 10 gp

    Feature: Wine Lets Secrets Out

    The vintner has a knack for storytelling and conversation. Through pouring a tasting and chatting they are able to learn a tale from the person’s past. Sometimes these are of an adventure, or a foible, or a mystery that needs to be solved, and at the rarest times these tales are things that were supposed to always remain hidden.

    Characteristics: For now, use those from the Guild Artisan or pick & choose your favorites. Whenever my background project sees full publication there will be unique characteristics for all of them.

    Vintner (2024/5.5e)

    Ability scores: Wisdom, Charisma, Intelligence
    Feat: Wine lets the secrets out
    Skill Proficiencies: Nature and one of Deception or Persuasion
    Tool Proficiency: Farmer’s Tools
    Equipment: Farming Tools, common clothes, 1 pound of cheese, 3 wine skins, 3 small cups or glasses, 10 gp (or 20 gp)

    Origin Feat: Wine lets the secrets out

    Aided conversations. When attempting to deceive or persuade a non-hostile creature and sharing a beverage you have advantage on the ability check.

    Pidgin: You have picked up bits and pieces of many languages. Select proficiency bonus additional languages in which you know some trade and casual phrases. You have disadvantage when making an ability check using this languages (or cultures).

    Vintner (Black Flag)

    Skill Proficiencies: Nature and one of Deception or Persuasion
    Additional Proficiencies: Farmer’s Tools
    Equipment: Farming Tools, common clothes, 1 pound of cheese, 3 wine skins, 3 small cups or glasses, 10 gp (or 20 gp)

    Talent

    You are familiar with the ways of farming and selling a product that often travels the region. Choose one of the following Talents to reflect that: Polyglot, Trade skills, Scrutinous

    By Jolbert

    This map popped into my Facebook feed the day I published the Vintner. It’s included because it is perfect, and actually reminds me of Balboa.

    Vintner Design Goals

    To more capture the feel of the pseudo-Mid Ages/Renaissance period the Vintner is the grower, the maker, the taster, the seller. While the Guild Artisan can capture this background, it forces the artisan into a guild. Many adventurers pride themselves in their independence. The Vintner had to be a solo gig.

    The choice of Deception or Persuasion is out of a desire to represent the different angles in marketing that can occur within the flavor business.

    When it came to tools versus languages there was a part of me that wanted a language rather than second tool, but that was hampered by two things. First, I generally frown on how D&D handles languages. Second, if I’m bundling growing in and have developed Farmers Tools, let’s use the Farmers Tools.

    The feature, which uses a Chinese proverb rather than the Latin In Vino Veritas, is an attempt to capture the flow of story and words as friends and even enemies commune over a bottle(s). As a DM having a player with this feature helps grant so many clues in new ways.

    Custom Backgrounds for 5th edition Dungeons & Dragons

  • Turning 5e Background Features into 5.5e Feats

    Turning 5e Background Features into 5.5e Feats

    Much of the flavor of the 2014 version of 5e Dungeons & Dragons backgrounds was within their features. These mild mechanics usually made some element of either the social or exploration pillars of the game.

    They’re gone, replacing both story and the two minor pillars with a Feat in 2024 D&D. It’s a shame.

    Many of my own custom backgrounds sit dormant, because the story was a key part of why they existed. And adding power through a Feat that offers more combat utility is silly.

    There’s a solution. The example comes from the Realms books. The Feats there ooze flavor in ways the Player’s Handbook does not.

    How can I do that at scale for the 20+ backgrounds I’ve created?

    Borrow from themes

    Find the origin feats (or talents) that are most similar to the desire and calibrate from there. Skilled, Musician and Crafter are the ones in the 5.5 Player’s Handbook I’ll lean towards. Black Flag expands the calibration in similar ways to the Realms books. Psychanist, Ritualist, Athletic, Polyglot, Scrutinous, and Trade Skills will be referenced as well. Having a bank of ten feats and talents to calibrate against should help.

    Walkthrough

    Let’s start with the clothier/weaver, which by design leans into tropes around various fictional cults that use threads to see futures.

    The original feature with mild mechanics.

    Feature: As the Wheel Wills

    You have a certain comfort and understanding that you aren’t always in control. You have advantage on saves against fear, charm and other enchantments after the first round in these conditions.

    Additionally, you are able to find and protect secrets. When using Insight or Sleight of Hand to keep or discover secrets you do so with double proficiency.

    Making it modern

    From mild mechanics to direct mechanics is a first step. The second is to calibrate versus similar feats and talents. As the Wheel Wills feels like more of a social feat with hints at magic, but not spell craft. Ritualist, Musician and Athletic have some of the heft I’ll use.

    As the Wheel Wills for 5.5e

    Due to your understanding of the wheel you have advantage on saving throws against fear and charm after being under the condition for one round. (This is somewhat similar to Athletic)

    Also, your experiences understanding that weaving is a physical representation of the connections between peoples you have expertise with one of Insight or Sleight of Hand. (Removing the more situational impact from the previous version).

    Another example – Cabbie/Ferien

    The Cabbie is an attempt to capture some Shadow & Bone, Narnia, Bridgerton, Gilded Age vibes.

    Feature: Talk too much

    You are a skilled conversationalist that frequently goes on and on. These long talks are often consuming and distracting. Some cabbies and feriens may have allies who use that speech as a distraction to pick pockets or similar events.

    Additionally, you pick up the streets, rivers or flyways of a new city quickly almost never getting lost in natural urban areas.

    Let’s convert that

    Origin Feat: Talk Too Much

    When talking to creature with which you share a language (or culture) you are able to distract a non-hostile creature. An ally attempting use Sleight of Hand, Stealth, or Deception against that creature has advantage in the current minute.

    Additionally after spending an hour in a bar, market, restaurant or other third place in a new non-magical urban area you are unable to get lost.

    Moving forward

    For some reason, unlocking this process within my mind is fuel to move forward with the backgrounds that are necessary to move forward with Uprising & Rebellion into the 5.5 era.

    Converting 20 was overwhelming until these thoughts. Plus, with the idea that an Origin Feat can be a General Feat with the addition of an attribute bonus that helps advance the three pillars I’m most interested in — Social, Exploration, Scheming. Because a few of these backgrounds and their newly associated Feats will unlock crafting, business management or militia actions.

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  • Using word-maps for quick reference during your games

    Using word-maps for quick reference during your games

    You don’t have to be a map maker to make adequate maps for gaming. A map can be as simple as showing the relative relationship between distance and location of the important elements. Even putting a few words on a page can be a map.

    Take the word map of the Six Kingdoms. It shows the relative locations and rough distances between the various kingdoms, their major cities and the other lands that interact in the World of the Everflow.

    Word maps can also represent a homestead, village or neighborhoods of a city.

    The image shows a group of seven index cards laid out on a speckled stone surface. Each card features a grid pattern and contains handwritten text in pencil. On the top left, there is a small vertical card with "Path" and "Divide" written along its edges. Adjacent to it on the right is a horizontal card labeled "Path of Dreams" with "Prairie" and "Auntie Houses" along the sides. Below are three more cards: the left card reads "Prairie" and "Auntie Houses," the middle card reads "Spine Bloom Common," and the right card says "Upper Rice Marsh." The bottom row features two horizontal cards, one labeled "Thunder Maker River" and the other, "Lower Rice Marsh." A pen with a black grip lies horizontally above the cards to the right.

    Any player can take a quick glance and know what each location is and what they connect to within the compound. More thorough descriptions in a blog post and in the character’s notes, but these quick notecards reminds us of Spinebloom Farms at the table.

    The image is a hand-drawn sketch on lined notebook paper, depicting a rough map layout with various labeled areas and arrows indicating movement or direction. The map is oriented with "Up Hill" on the left and features several labeled sections, including "Upper Hillside," "Lower Hillside," and "Rolling." There are geometric shapes, such as squares and circles, possibly indicating buildings or points of interest, with some labeled "Upper," "GLAV," and "Verde Breezde." Lines and arrows point toward different labeled areas like "To Telee" and "Esedelens Tavern."

    Fort Ooshar is a bridge-town that turned into a fortress when Sheljar fell to the Necromancer. This quick sketch lays out the neighborhoods of the bridge-town, the gates, the fields and the nearby hills.

    Yes, a better mapmaker would be better. My favorites are Deven Rue and Dyson Logos. I support both via Patreon and use their works in my games.

    But sometimes I want something that is unique to my world. That leaves me with my lack of art. I then build a word map.

    Keys to making a quick word map.

    1. Decide on the central space
    2. Build outward using relative distance to represent a unit of time
    3. Include evocative names, especially when in tight focus
    4. If building a dungeon, point crawl or town having connective tissue — this can be a road, river, or other path
    5. Leave yourself space to build details and add discoveries

    Doing this as a player

    Old school D&D involved at least one player making highly detailed maps. But a word map may be all that’s necessary to prevent your party from getting lost. Using a room-and-halls word map by the player helps represent how the characters think.

    In essence you are channeling the concept of ‘turn left after the big red barn, go over Herringbone Bridge, take the third path’ into a simplistic drawing.

    These are quick, simple and can be done on a 3-by-5 card or as a sketch in something as simple as Paint, Slides, Canva or even in a Spreadsheet (the Six Kingdoms started as a spreadsheet).

    One of the special powers of the word map is that they’re quick. You don’t need to search for anything. It’s a sketch that can be done in a few seconds.

    Whether as a player or a DM this tool can help you understand your fantasy world better than without a map at all.

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  • How my campaign changes when a new product drops

    How my campaign changes when a new product drops

    The recent addition of Drops subscription content to DnD Beyond is going to challenge me.

    I’m running only a single intermittent 5e campaign right now. The Ferments uses 2024 as its base set, but permits things from Black Flag, 2014 and A5e in general, with a quick scan to make certain that the addition fits within the campaign themes and the setting’s common lore.

    In the past it’s been easy to judge what works and doesn’t. Book releases are heavily themed. Most grimdark will not fit in The World of the Everflow. Dragon stuff always fits. Giant stuff rarely fits. The new dinosaur book added to Beyond fits well in an undiscovered-to-this-point land.

    But now there are weekly drops. The player facing stuff needs a quick review. Maps and stickers won’t matter because we aren’t using the Maps VTT. The cosmetics are fine, because they help a player connect with their character.

    Teos explains the broader program.

    Evaluating the content to fit The Ferments and The World of the Everflow

    First off, the five feats added are all extra planar in a way that has not been explored in our games through the several hundred sessions of play plus writing and backstory. There’s only been a single Warlock.

    Those are going to be easy to ignore. If I could toggle them off at the campaign level I would.

    • All five feats = no
    • Pact Seeker background = with lore tweak and different feat
    • Astral Flood = yes, fully
    • Buzzing Bee = yes, fully
    • Insidious Rhythm = yes, fully
    • Leomund’s Lamentable Belaborment = yes, fully
    • Sticks to Snakes= yes, but DM content only

    The Pact seeker background doesn’t fit as written. The lore doesn’t work because of the demand that the pact is extraplanar, but if a player wanted to rework that and take a new origin feat it would be allowed. Maybe they are seeking a pact with a religious figure, an elder dragon, a scholar or something similar.

    There are also five spells in the first Drops.

    Astral flood fits unchanged. The Astral and Ethereal are somewhat merged in my world and opening that up to the physical realm would be devastating.

    Buzzing bee is excellent. My first encounter with Bee was the useless cantrip from Unearthed Arcana back in the 80s. This is better and needed. It fits the use of animals for the Kin too.

    Insidious Rhythm is a fun spell too. The magic of performance by Bards and others would be the path of introduction.

    Leomund’s Lamentable Belaborment may not fit combat well. It does fit in social and political settings. Players will definitely find a way to turn a crowded room into a debate-disaster.

    Sticks to Snakes is a classic spell, but this version is quite underpowered for 2024. It adds in-combat complexity for low damage. It reads more like a 2nd level spell and not a 4th. For narrative purposes it fits the world well. But it’s a waste for a player. This will be DM content only.

    Eleven player facing items this week needed to be reviewed. Next week there will be more. And then there will be more. And more.

    It’s going to be too much.

    And each drop and each book from every publisher stretches and pushes a world. But fantasy worlds are not only defined by being permissive. They are also defined by what’s forbidden.

    Every world a DM and their tables creates can choose to be a global fantasy (kitchen sink) or be as neatly defined as the group wants.

    With Drops the default in the Everflow will not be for permission, but to evaluate what a player wants to add as they want to add it in order for us to continue to explore the themes of the world — how strong can the love between person and animal be, who gets to control access to knowledge, how can our local connections make the world better for most.

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