d&d 5e: roadside backgrounds

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Page 2: D&D 5E: Roadside Backgrounds

You are a travelling combatant, always on the lookout for

a new challenger. You duel with those who seem

competent enough to push you further. You might use

swords, magic, or even games of chance to test yourself

and your chosen foe. In the end there is nothing more

important to you than proving of your mettle.

Skill Proficiencies: Insight, Intimidation

Tool Proficiencies: One type of gaming set

Languages: One of your choice

Equipment: A token of favor from an admirer (a

handkerchief, flower, or love letter), a set of bone dice or

deck of cards, a set of traveler’s clothes, and a belt pouch

containing 12 gp

Your reputation and bearing as a duelist compels others to

accept your challenges. So long as you offer them a duel

while outside of combat, most NPCs who are not utterly

outclassed by your Level are willing to have a go with

you one-on-one, without the help of their companions or

bodyguards. Foes are usually willing to duel until first

blood, but some are even up for a fight to

unconsciousness or death, particularly if you’ve really

angered them.

Duelists are defined by their need for adventure, a

challenge, and the freedom to roam the world in search of

these things. They value the ability to do things their own

way and often have a past which reflects escape from a

stiflingly rigid situation. Yet they see the duel as a pure

expression of skill, and highly revere fairness in such

competitions.

d8 Personality Trait

1 I treat nearly every endeavor as a competition.

2 I seek out peers and distain my inferiors.

3 I think I’m a celebrity and act as though I’m

constantly recognized.

4 I find it extremely embarrassing to give up or

surrender.

5 I keep my weapons and armor meticulously

maintained.

6 I have a trusty weapon I can’t live without.

7 I give combat pointers to nearly everyone I meet.

8 I claim to have never been beaten in a duel.

d6 Ideal

1 Danger. It is the threat of death that lets us know

we’re alive. (Neutral)

2 Defense. The weak must be protected by great

champions. (Good)

3 Fairness. Competition done fairly is the only

way to know who’s best, or who is favored by the

gods. (Lawful)

4 Freedom. Never let others dictate the terms of

your existence. (Chaotic)

5 Glory. Notoriety brings with it all the pleasures

the world has to offer. (Evil)

6 Self-Knowledge. Only by constantly testing

your abilities can you know your worth. (Any)

d6 Bond

1 I shall never cheat in a duel.

2 I will become the greatest duelist in the world.

3 I will always make for the most dangerous foe.

4 I’ll prove my old masters wrong and accomplish

great things.

5 Upholding the honor of my house, family, nation,

or friends is of the utmost importance.

6 Defeat is not an option.

d6 Flaw

1 I can be goaded into a fight rather easily.

2 I will not strike an unwary or unarmed foe.

3 I think battle is the solution to every problem.

4 I think I’m the best combatant in the party and

integrate this into my strategies.

5 I have no problem going off alone into danger.

6 I am easily seduced, especially by those who can

fight or otherwise compete with me.

Page 3: D&D 5E: Roadside Backgrounds

You are a special kind of vagabond, one who spreads

wisdom and foreknowledge to those who seek comfort in

this world. Bearing omens and advice, you are born for

the open road, constantly in danger of angering those to

whom you’ve dispensed truth. You must always look for

new horizons, bringing a little insight into the workings

of the cosmos wherever you wander.

Skill Proficiencies: Insight, Performance

Tool Proficiencies: Fortune telling tools

Languages: One of your choice

Equipment: A mule, a set of fortune telling tools (cards,

dice, tea leaves, etc.), a set of common or costume

clothes, and a belt pouch containing 5 gp

Once per day you may attempt to use your fortune telling

tools to determine the near future of someone who has

come to you for advice. You learn vague impressions of

this future, such as danger, love, loss, or betrayal. You

may even use this Feature to discover your own future.

Alternatively, you may use this Feature to give your own

Inspiration to another PC, while doing a reading for them.

Fortune Tellers live lives that are intertwined with fate.

They understand that everyone has a role to play in the

future, and usually come to accept their own. This

acceptance leads them to a kind of serenity in the face of

danger, with the ability to act quickly when their

supposed destiny presents itself.

d8 Personality Trait

1 I hate to stay in one place for more than a day or

two.

2 I speak mostly in cryptic phrases.

3 I believe strongly in destiny, accepting all events

as meant to be.

4 I am from a far away or minority culture, with

ways that confuse others.

5 I have discovered that my own future is to die

horribly or heroically, and I accept that.

6 I know that fortunes can change and seek to make

the world better.

7 I dislike games of chance; they treat fortune as a

trifle.

8 I have seen a coming war or apocalypse.

d6 Ideal

1 Community. Those you travel with are your

family. (Lawful)

2 Curiosity. What comes over the next hill is

worth seeing. (Any)

3 Hope. The future holds much that is positive.

(Good)

4 Independence. Carving out your future means

submitting to no authority but your own.

(Chaotic)

5 Survival. Fulfilling your destiny means living to

see it at all cost. (Evil)

6 Wisdom. Acting without concern for the future

is foolish. (Neutral)

d6 Bond

1 I shall fulfill my destiny.

2 I will always tell fortunes truthfully.

3 I can never settle down in one place.

4 The plan of the gods must become known.

5 My wisdom comes at a price to those who are not

my companions.

6 The evil forces in the world must be stopped.

d6 Flaw

1 I find it hard to trust people who are not my

traveling companions.

2 I will stop at nothing to fulfill my own destiny, or

that of the party.

3 I am condescending to those who are not wise.

4 I often tell fortunes that are merely what people

want to hear.

5 I act like I know the future, even when I don’t.

6 I often lie to authority figures and would never

come to them with a problem.

Page 4: D&D 5E: Roadside Backgrounds

You are a devout adherent of a particular god or faith,

proving such by journeying to places of importance for

your religion. Through conviction and grit you will come

to see the locations most celebrated by your people.

Along the way you’ll likely get into adventures, the better

to test your devotion.

Skill Proficiencies: History, Religion

Languages: Two of your choice

Equipment: A holy symbol, a set of common clothes,

and an alms box containing 15 gp

You know a number of routes, points of interest, and

places to stay along the way to various religious sites

throughout the known world. You can usually find cheap

lodging, shortcut roads, and other useful advantages when

on a journey, so long as you are somewhat near a

pilgrimage site for your religion. Sometimes you even

know bits of trivia about the area, usually relating to your

god.

Pilgrims are defined by their devotion and take pains to

prove it. At the same time they are sightseeing tourists,

initially along for the thrill of adventure and the supposed

importance of their holy journey. They are a strange mix

of thrill-seeker and pious devotee.

d8 Personality Trait

1 I have seen many strange things on my journeys

and enjoy telling tales.

2 I find it calming to live a simple lifestyle with

few possessions.

3 It’s important for me to spread the word of my

god to all, especially those of other races and

cultures.

4 I believe my god speaks to me in my dreams.

5 Though I seem pious, I often break my vows

when tempted.

6 My journey is holy and I try not to profane it with

revelry or unnecessary violence.

7 No one is more devout than me. No one.

8 I’m not actually all that devout; I’m just out here

for the adventure or in order to escape my family.

d6 Ideal

1 Courage. Sometimes you must do what must be

done, no matter the consequences. (Chaotic)

2 Expansion. You must make sure your god is the

most powerful one, revered at many sites. (Evil)

3 Generosity. Others should benefit from the

fruits of your blessings. (Good)

4 Humility. One must hold themselves to the

highest standards before judging others. (Neutral)

5 Tradition. We have a place in the continuity of

history and we should honor the past. (Lawful)

6 Wonderment. The world is full of inspiring sites

and moments of incredible beauty. Find them.

(Any)

d6 Bond

1 I will visit every major pilgrimage site my people

hold dear.

2 No temptation will seduce me from my vows.

3 The weak must be protected.

4 I am not worthy of riches.

5 Non-believers shall not foul the sites of my faith.

6 I must prove my faith in some way before I die.

d6 Flaw

1 I am at times hostile to those not of my faith.

2 I take foolish risks because I think I’m being

tested by my god.

3 I hold my own wisdom above that of others.

4 I am overly curious and concerned with the

private lives of others.

5 I hold to tradition at the expense of adaptability.

6 I’ll do anything to protect the reputation of my

church.

Page 5: D&D 5E: Roadside Backgrounds

You are an explorer, route finder, and cartographer for

your nation, people, or merchant company. You’ve spent

time trekking out into the world to find unexplored

regions and unknown peoples. You’re someone who

loves being first to see or do something, and your attitude

helps to find safe passage for those who follow in your

footsteps.

Skill Proficiencies: Athletics, Perception

Tool Proficiencies: Cartographer’s tools, navigator’s

tools

Equipment: Cartographer’s tools, navigator’s tools, a

map case, a map of the local region, a set of traveler’s

clothes, and a belt pouch containing 10 gp

You are capable of plotting a route to nearly any

destination, no matter how remote. If you’ve heard of it,

you can find a way to get there. The more obscure the

location however, the more likely it is your journey will

take you through dangerous regions.

Trail Blazers are defined by their adventurous,

exploratory attitudes. No location is too remote; no

danger too great. This doesn’t mean they don’t take

precautions on a journey, but it does mean they’re usually

up for anything that sounds exciting.

d8 Personality Trait

1 I love to be the first in the room, first out the

door, first watch, etc.

2 I’ve seen so many places that they all blend

together for me now.

3 I often attempt to speak languages I don’t know.

4 I can be cavalier and reckless when exploring

new places.

5 I was the first to discover something important

and well-known.

6 I’m obsessed with haggling and getting a good

deal in trade.

7 All of my maps are works of art, lovingly crafted

after a great deal of work.

8 I’ve met many interesting people in my day, seen

many amazing things, and I enjoy regaling others

with the tales.

d6 Ideal

1 Adventure. A hero must always be getting into

danger. (Chaotic)

2 Commerce. Trade is mutually beneficial for

everyone. (Lawful)

3 Culture. Learning about others reveals

important qualities in us. (Good)

4 Discovery. The world must be explored. (Any)

5 Initiative. Being first to do something secures

your legacy. (Evil)

6 Optimism. Even violent encounters with native

cultures will eventually lead to good things in the

long run. (Neutral)

d6 Bond

1 I shall never stop discovering new things.

2 Whenever I find a new place, I’ll leave a marker

or map a route so that others may come this way

more easily.

3 I’ve seen something amazing and I’ll never tell a

soul about it.

4 I will always support the druids and rangers of

the world.

5 The cultures I find should be dealt with equitably,

not exploitatively.

6 I’ll draw a picture of every interesting thing I

encounter.

d6 Flaw

1 I over-plan every endeavor.

2 I under-plan every endeavor.

3 I am overly loyal to the merchant company I

work for.

4 I leave a trail of markers wherever I go, making

me easy to track.

5 I “go native” whenever I encounter a new people,

adopting their ways.

6 I often underestimate the amount of time it takes

to get somewhere.

Page 6: D&D 5E: Roadside Backgrounds

A seeker of fortunes, mostly lost and hidden in the ruined

places of the world, you are bravely greedy. You’re

undeterred by such things as traps, curses, and eternal

servitors and as often as not you solve the mind bending

riddles and puzzles that block your passage.

Skill Proficiencies: Investigation, History

Tool Proficiencies: Thieves’ tools

Languages: One of your choice (usually an ancient

language)

Equipment: Thieves’ tools, a grappling hook, 50 feet of

hempen rope, a set of traveler’s clothes, and a belt pouch

containing 10 gp

You are a master of solving puzzles, cryptograms, and

mathematical problems. Whenever you are faced with a

logic-based task barring your ability to proceed in a

dungeon or other treasure site, you may ask your DM a

single yes or no question about the nature of the problem,

and they must answer. This question cannot be so

specific that it would ruin the puzzle, but it can be one

that eliminates a number of possibilities or leads you

directly down the right logical path.

Treasure Hunters are by their nature seekers of material

things. This does not always mean that they are miserly

or even hedonistic. There are many reasons to be tempted

by the thrill of old and dangerous places. Many reasons

to need coin.

d8 Personality Trait

1 I’m obsessed with things from a prior age,

collecting many relics from that time.

2 I studied history academically, apprenticed to a

famous scholar.

3 I need wealth in order to protect my loved ones.

4 Treasure gives me the thrill I need to feel alive.

5 I wish to see the world, so I hunt treasures that

take me to foreign places.

6 I’m constantly describing the historical

significance of everything I see.

7 I have a rival who seeks to thwart my endeavors.

8 I seek treasure to pass the time as I flee my

troubled past.

d6 Ideal

1 Greed. Treasure is its own reward. (Evil)

2 Drive. Goals define our existence. (Neutral)

3 Cunning. Outsmart the past. (Any)

4 Flexibility. Stay fluid and think on your feet.

(Chaotic)

5 Restoration. Some things belong in a museum.

(Lawful)

6 Reverence. Have a place in your heart for the

people who inhabit the past. (Good)

d6 Bond

1 I will discover the truth hidden in the ruins.

2 No trap can stop me.

3 I shall earn the fame I deserve.

4 I can’t leave any treasures behind.

5 I’ll learn something nobody knows before I die.

6 Every puzzle must be solved.

d6 Flaw

1 I constantly speak in riddles.

2 I’m more concerned with treasure than people.

3 I think I deserve all the glory.

4 When working on a puzzle, I stop noticing

everything else around me.

5 My mentor died trying to solve a particular

mystery and I’m obsessed with following in their

footsteps.

6 I often forget to plan an escape route out of the

dungeon.