• Justin Handlin

Dungeon Dressing: 20 Festival Games and Events to Find in your Dungeons & Dragons Game



The fantasy world is one of adventure, magic, and monsters. When a character decides to step into the life of adventuring, it becomes one of almost all business. Chasing down bandits, slaying beasts, and saving towns from natural and magical disasters. While the heroes are hard at work, the world moves on with its daily life. The holidays and yearly festivals come and come on a regular basis. When was the last time your adventurers were in a town during a festival celebration? Consider for a moment the revelries and excitement this sort of event brings to local farmers and merchants. Fairs and Festivals are powerful tools to help bring your Dungeons & Dragons games to life. We’ve included some sample rewards, but feel free to change, or enhance them with your own unique rewards.


Get 20 fantastic games and events that you can use in your Dungeons & Dragons games.


20 Festival Games and Events to Find in your Dungeons & Dragons Game

  1. An elderly man stands taunting strong-looking ladies and lads to try out his hammer strike game. A tall pole has a smooth sphere attached to the pole with a lever and target at the bottom. Running along the pole are markings with strength ratings. Each tier requires a successful Strength Athletics check to reach. The higher the tier, the better the prize. Farmer Tier: DC 10, Soldier Tier: DC 13, Green Adventurer: DC 15, Heroic Adventurer: DC 18, Legendary Might: DC 22. A character earns a unique emblazoned badge for the highest tier they reach.

  2. A large stage is set up with what appears to be a living space. Furniture and common household items clutter the small area. Two large curtains hang from each side of the stage. An older raven-haired woman with silver streaks runs the stage with her grandchildren. “Interested in playing Mama’s Memory? A simple game really. We close the curtains, the kiddos add and remove objects from the room and then you let us know what is missing.” The character must succeed on a DC 15 Intelligence (History) check. A character must succeed on three checks before acquiring two failures. The winner is given a golden badge with bright sun embroidered on it. If the characters acquire two failures the young children laugh and insult the character's intelligence.

  3. A slender, middle-aged woman with copper hair tends to a set of targets that swing back and forth, each farther away than the last. Characters must throw daggers or handaxes at each of the moving targets. The character must succeed on an attack ranged weapon or thrown weapon attack roll. The character has 4 pieces of ammunition. The AC of the first target is 10. The AC increases by +5 for each target beyond the previous one. A prize is awarded for anyone who can hit 2 or more targets. The winner earns a dagger forged of glass.

  4. A barrel-chested long face man with black hair pulled into a ponytail under a large brimmed hat stands just outside a large fenced-in area. Inside a massive bucking bronco. “Do ya ride? Ol Tanner here is a tough one. Current personal best is 9.9 seconds before Tan threw me off. Think you can do better?”. The goal here is for the character to sit atop the muscular beast for more than 10 seconds while it bucks, twists and flails. A character must succeed on DC 10 Strength (Athletics) or Dexterity (Acrobatics) check. The DC increases by +5 for each check beyond the previous one. The character must succeed on three skill checks before acquiring two failures. The character must make a contested Wisdom (Animal Handling) check against the bronko's +7 to his Wisdom (Insight) check. On a success, the character has Advantage on one of the rolls. A character who succeeds is awarded the title “Branco Buster”. On a failure, they fall to the ground with a mouth full of dirt.

  5. Three young children of maybe 12 years of age call out to any who are willing to test their agility. The game is one of dexterity and nimbleness. A creature must climb to the top of the 80 foot angled rope ladder while it is being twisted and shaken by the young lad and his friends. The character must succeed on a DC 15 Dexterity (Acrobatics) check. A character must succeed on three checks before acquiring two failures. The winner earns a new pair of flexible shoes perfect for climbing and balancing. If the characters acquire two failures they fall off into a pool of mud below the ladder.

  6. A stout man sits near a large basket of dozens of chicken eggs. He shouts to any passerby. “Hey, you there! You look like someone who has picked up more than a few books. How would you like to guess the number of chicken eggs inside this basket? The closest guess to the right amount wins a prize. But you only get one guess per person. We will be deciding the winner based on who gets it closest later today.” A character who succeeds on a DC 21 Intelligence (Investigation) check succeeds at the challenge. If multiple characters succeed, then the highest roll wins with the exact number.

  7. A young man with messy golden hair shouts to the crowd. “Step right up! Show our judges what you’re made of! Show us and your crowd your talent. Your talent may be good enough to win you a fantastic monetary prize as well as a certificate identifying you as “The Talented”. A character who partakes in the talent show must succeed on five DC 14 Charisma (Performance) checks before acquiring three failures. A character who fails a check by 5 or more begins getting booed from the crowd and having vegetables toss at them.

  8. A small half-round table. On one side sits a willowy man with a braided beard with a deck of cards. “Want to sit down for a few hands? A game of skill, and a bit of luck. Ain’t nothing better.” The poker table is treated like a game of yahtzee. Each player rolls 5d6s that represents a hand of cards and must get the highest score at the table. Each character can make two rerolls. Each roll can include any number of dice. But they only get two. A character can roll a DC 18 Dexterity (Sleight of Hand) check. On a success, they can reroll a single dice.

  9. Several long tables with small personal cooking fires around each fill the area. A large plump man with red hair and mutton chops with a white apron and chef’s hat welcomes all to his tables. His challenge is one of preparation and cooking. The character must succeed on a DC 15 Wisdom (Survival) check using the cooking utensils. A character must succeed on three checks before acquiring two failures. If the characters acquire two failures the chef tells them “This food you have prepared. Never, ever serve this to another living person, lest they die of dysentery.”

  10. An elven beauty with fair skin and emerald hair runs a booth filled with dozens of bottles in a series of rows. “Welcome to the ring toss. The rules are simple. The rings will fluctuate in size. You must not only achieve an understanding of the pattern but must also accurately throw them to land upon the neck of the ale bottles. Should you succeed I will bestow upon you the title of “Linte Saira” meaning Wise and Swift One.” Because the rings change sizes the characters must succeed on a DC 18 Intelligence (Investigation) check and an improvised weapon attack roll, AC 18. If the character fails either roll they lose the game. If they roll a natural 20 on the attack roll, they succeed automatically.

  11. A towering elderly man with a beard down to his knees sits upon a barrel outside of a large tent. The room is a house of mirrors. The characters must navigate their way through the complex maze. The only problem is that each maze is a trained mimic. Once the characters enter, the mimics move around when the characters aren’t looking. Making the puzzle that much more difficult to solve. The characters must make a DC 10 Intelligence (Investigation) or Wisdom (Perception/Survival) checks. As the mimics move around the DC increases by +5 for each check beyond the previous one. The characters must succeed on four skill checks before acquiring 2 failures.

  12. A woman with wrinkly skin and a large wart on her nose sits alongside a collection of alchemic vials, baubles, and a variety of herbs. “Welcome. Do you have an interest in the creation of poultices? I teach the creation of special medicines as I travel to those who wish to learn.” The character must spend their entire time at the festival in this event to gain the benefit. A character who partakes in the crafting event must succeed on five DC 16 Intelligence/Wisdom (Nature) and/or Intelligence/Wisdom herbalism tool checks before acquiring three failures. On a success, the character successfully creates a level-appropriate potion of healing. This potion automatically heals the maximum amount. On a failure, they create a potion of healing that automatically heals for its lowest amount.

  13. In a large muddy pit sits a greased-up gnome painted with green skin and fake pointy goblin ears. The gnome shouts “Hehe, you can’t catch me!”. The goal is simple, to catch the fake goblin as it runs around the slick pit. The character with a speed of 60 feet has Advantage on grapple checks. The chase begins with the character making a DC 13 Dexterity saving throw. On a failed check they struggle with the slickness and have Disadvantage on the grapple check. The character must then make a contested grapple check gnome’s +7 to its Dexterity (Acrobatics) check. If the gnome is caught, they give the character the title “Slick Swift”.

  14. At the center of a small field of flowers sits a dryad. “Do you know the touch of the wild mother?” The dryad challenges the character to identify all the flowers, plants and tree bark presented to them. A character must succeed on DC 10 Intelligence (Nature) check. The DC increases by +5 for each check beyond the previous one.The character must succeed on three skill checks before acquiring 2 failures. A character who succeeds is offered up to 10 berries created from a special goodberry spell ritual. These lose their potency if they have not been consumed within a tenday.

  15. A halfling sits atop a stump with a collection of material spellcasting components such as a piece of cured leather, a rod of amber, bat guano and more in front of her. “Know your spells do ya? Well, the game is simple. I show you a component, and you name the spell that it goes to. Got a special gift for ya if ya do well.” A character must succeed on DC 10 Intelligence (Arcana) check. The DC increases by +5 for each check beyond the previous one. The character must succeed on three skill checks before acquiring 2 failures. A character who succeeds is offered a special material component called a star rose crystal. When used as an additional component to a spell, the spell is cast as if it was cast with a spells slot of 1-level higher than the slot expended, up to a maximum of 9th level. The star rose is consumed.

  16. A slender man with a bow slung across his back stands at the end of a forest clearing. “Ya here for the hunt!? If so, you’ll find tracks inside of a variety of beasties from the wild. Identify them properly to win. Easier than trapping an owlbear I say.” A character must succeed on DC 10 Wisdom (Survival) check. The DC increases by +5 for each check beyond the previous one. The character must succeed on three skill checks before acquiring 2 failures. A character who succeeds is offered the title of “Master of the Hunt” and a small necklace with owlbear tracks stamped into it.

  17. A mountain of a half-orc with a broken tusk and arms the size of tree trunks sits at a table with a single seat across from her. “Ha! I’ve seen kobolds with bigger arms than you. Shedok can beat you with eyes closed and mouth full of food.” The half-orc strong arm contest is one of brute strength. The character must make a contested Strength (Athletics) check against the half-orc’s +7 to her Strength (Athletics) check. The game is played, best two of three rounds. A character who wins is given the title “Strongarm”.

  18. A sly man with a loose white shirt, knee-high boots, and a cutlass strapped to his side stands behind a table with five large cups and a copper nugget. A character who succeeds on a DC 10 Intelligence (Investigation) check confirms the nugget is real copper. “Looking to keep your eye on the prize? The rules are simple. I place the nugget under a cup and move it around. If you can pick the cup that the nugget is hidden under, it’s yours. What do ya say?” A character must succeed on DC 10 Wisdom (Perception) check. The DC increases by +5 for each check beyond the previous one. The character must succeed on three skill checks before acquiring two failures. The character must make a contested Wisdom (Insight) check against the slyman's +7 to his Dexterity (Sleight of Hand) check. On a success, the character has Advantage on one of the rolls. A character who succeeds is offered the copper nuggets as a reward. If the character failed the contested check, the copper nugget is a fake.

  19. A thick rugged dwarf with silver hair, and a braided beard down to his belly stands at a table with several empty seats. “Aye, ya lookin to down a pint with a stranger? If ya can outlast me, there might be something in fer ye. Can ye hold yer drink? I’ve got some bourbon toe to tickle yer tongue.” This is a contest of resilience and stamina. A character must succeed on DC 10 Constitution saving throw. The DC increases by +5 for each check beyond the previous one.The character must succeed on three skill checks before acquiring 2 failures. Each failure gains the creature a level of exhaustion. A character who succeeds is offered the title of “Iron Gut”.

  20. An athletic middle-aged man with brown hair tends to a set of targets spread apart in a long line, each farther away than the last. Characters must shoot arrows from a bow at each of the moving targets while riding on horseback. The character must succeed on an attack ranged weapon weapon attack roll. The character has 4 pieces of ammunition. The AC of the first target is 12. The AC increases by +5 for each target beyond the previous one. The character can make a contested Wisdom (Animal Handling) check against the horse's +5 to his Wisdom (Insight) check. On a success, the character has Advantage on one of the rolls. A prize is awarded for anyone who can hit 3 or more targets. The winner earns a black leather arrow quiver and a matching shawl. Embossed on the leather are the words “Hunter’s Pride”.

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