One hundred fun games and booths for your players to explore at the local faire.
An Axe-Throwing (or similar projectile) Contest. (Dexterity Check)
An Archery competition. The contestants are trying to shoot an apple off the head of a gnome. (Dexterity Check)
Raffle Lottery. 1gp to enter!
A great Tug of War over a pit of mud. (Strength Check)
A booth disguised as a pie stall that buys and sells illegal goods (drugs, banned religious symbols, etc.)
Arm Wrestling Contest. (Strength Check)
A Pick Pocketing Challenge. Everyone attending the fair is given a bright piece of cloth to be put in their belt/pocket. If you keep hold of yours, you win a prize at the end of the day. If you are able to pickpocket other people's cloth, then you could win the grand prize. (Sleight of Hand Check)
An ale-drinking contest. (Constitution Check)
Fencing with wooden swords. Three hits, and you're out! (Standard Combat Rules)
Lockpicking contest - while blindfolded! (Thieves Tools Check)
Rope Climbing Competition. (Dexterity or Strength Check)
A Log Balancing contest. The winners of the contest face off in a pool filled with water elementals. (Dexterity Check)
A music contest between individual performers or 'bands'. (Performance Check)
Bull riding contest. Stay on the longest to win! (Athletics or Strength Check)
A scavenger hunt. A special golden coin has been hidden somewhere on the fairgrounds. Can you find it? (Perception Check)
Lumberjack Games. Who is the fastest at chopping these massive logs? (Strength Check)
Exotic Animal Show. Come see fantastical animals from all across the realm!
Animal races. Which one do you bet on to win the race?
A man dressed in a jester costume is sitting above a dunk tank. Can you hit the target?
Horse Racing. Race against some of the most experienced horse-riders in the realm! (Animal Handling Check)
Gambling/Card/Dice Games. This is most likely illegal, so they take place in a closed tent in the back of the fair.
The Big Hammer And Bell Contest. (Strength Check)
House of Mirrors. Can you escape? (Perception Check)
Jousting on Horseback. Can you knock your opponent off their horse? (Animal Handling and Dexterity Check)
Every year, a particularly skilled Minotaur makes a hedge maze. She is a gardener and spends the season making labyrinths for the townsfolks festival. There is a plate of cookies in the center, and her calf (young son) is patrolling inside to help people who become lost. The Minotaur charges 1 copper for entry, and donates the money to charity.
Bobbing for apples. Some apples are injected with a polymorph potion.
Liar's Contest: spin the wildest tale you can think of and the crowd votes on the best one based on believability, complexity and incredibility. (Bluff/Deception Check)
The tent of 'long rests' in 20 minutes!
Prettiest Baby Pageant.
Deep-Fried Foods on a Stick.
Puppet show using Minor Illusion and Mage Hand.
A booth selling Potions of Thirst Quenching (water).
A bored-looking devil sitting at a booth with a sign saying 'Anything you want: $Your Soul'. Be very careful here, as what he offers starts out seeming great, but eventually is just terrible.
A “Guess the mimic” game. Players are brought into a fake house and must determine which object is the mimic. Maybe the mimic is the house itself? (Perception Check)
A Guess Your Weight stand.
A rogue favorite; Hide and Seek competition. (Stealth Check)
Cunning Linguists; replace a language at random (pick a random; non-common, language the player knows replace it randomly from a list as large as you want, if they crit, they keep their original language, if they crit fail, they lose their original language, and gain nothing)
Feat for Curse? (Your player can buy an extra feat, but they are stricken with a curse. Can be a strong curse or as simple as a new character flaw.)
Greased Pole Climbing contest - there's a tree trunk liberally coated in grease and the first person to reach the top is the winner. Everyone tries to climb at the same time.
There is a kenku hermit from the neighboring hills who has a large wagon filled with nuts and berries. They are selling a handfull for 1 copper each.
There is a wizard who is running a -make your own potion- stall. The wizard will help players make any potion they want at half price.
There is a beefy half orc chef selling 2gp firewater, an ale that gives +1 strength for 1d8 hours to anyone with a con modifier of +3 or higher.
The town guard is giving free fighting lessons for able-bodied citizens. There is a list where the festival goers write their contact information for the towns militia.
A gnome trinket master is making clockwork trinkets for the townsfolk.
The local Thieves Guild is smuggling cheap ale off the back of a wagon and will pay the party to help them carry the items before the guard comes back with a warrant.
The mayor is letting the winner of the children's foot race hit him with a custard pie.
There is a booth where town officials can be found. The booth is a guard station, water station, first aid station, lost and found, (one random item from the party can be found here) and fair management station. There is a donation jar. The officials have a few errands they ask of the party such as collecting late dues from some of the fairground shopkeepers.
A 'Fungeon' full of 'Funsters' and 'Treasure'. Look out for the 'Traps' and the pickpockets.
A literal haunted house of past carnival workers, so they know not kill anyone.
Gurning competition. (Seriously, it's a real thing. Compete to pull the most ridiculous face.) (Performance Check)
Living tower - teams of (your party size) need to build the highest tower out of their bodies. (Athletics Check)
A Fortune Telling Booth.
Cooking contest - player(s) need to prepare some exotic dish and the only thing they know is the dish name. (Cooking Check - and perhaps History, to see if they recognize the meal?)
Tag a Guard - you need to kick a guard and not get caught.
A table with bored guards looking for recruits, people are clearly walking around it.
A chess-playing chicken. 5 silvers to play, beat the chicken and double your money. (Intelligence Check)
Bake sale for the local orphanage.
Displays of the local children’s artwork.
Goldfish Scooping. Some say the goldfish are actually polymorphed fair-goers who were caught cheating some of the other games.
A divination stand with an old lady with a crystal ball... Or she reads the lines in your hands... Either way, it's up to the DM whether it's true divination.
A stall that sells mildly enchanted jewelry that can change colors at will.
A lavender-skinned tiefling does palm readings while their (Make both parties male or female, whichever you choose) dwarven friend polishes weapons and armor for people who are having their palms read.
A nearby tent displays various works of art. The artists are there for questions about their pieces.
A team of 3-5 people are allowed to compete in an eating contest against a local hill giant. The hill giant rolls 2d100. Each player rolls 1d20+Con. Whichever team's total is higher wins the contest. The party becomes fatigued for 24 hours if they compete.
A Magician. (No actual magic, just smoke and mirrors)
A Mead Maker's Competition. They're short a couple of judges, and will offer the job to anyone who looks to have a strong constitution.
A simple cloth is laid out in front of a famous local hermit. He magically mends objects and performs low level spells at a deep discount. He uses the money to buy supplies so he can avoid town the rest of the year.
A booth is staffed by students from a local magic academy. They take requests for magic assistance but can't really do anything themselves. An appropriate level mage will visit each customer within a few days. The students get a cut of the revenue towards their tuition, so they can be very pushy.
A Sparring Ring. Locals can take out whatever frustration they've had on each other over the past year here!
A Fancy Dress Competition. Tailors get to show off what they've been working on over the past year.
A small number of goblins can occasionally be seen sneaking around the fair, sometimes they will be spotted oh-ing and ah-ing at some of the attractions. If questioned, they flee. If found again later and questioned, they are doing research for their own Carnival.
There are temporary shrines from many different Gods and Goddesses. They can be prayed to for small blessings.
A group of local Living Trees are handing out apples and giving advice in their deep voices such as 'make sure you plant the seeds', and 'don't play with fire'.
A group of Yuan-Ti have set up an exotic (lightly cursed) amulet shop.
Some sprites and pixies are letting people fly in exchange for hunting equipment. They have a large furnace with a baby firenewt inside where they dispose of the hunting gear.
The town guard is hosting a make-your-own banner booth. An enchanter can be hired to enchant the banner.
There is a costume booth where a master tailor, doppelganger, illusionist, and thief work together to give anyone a makeover, haircut, or costume of their choosing.
Exotic pet rock dealer. (1 in D8 rocks is an elemental pet!)
There is a Slap-a-Guard booth. Once a year, the citizens can pay 50gp to slap a guard in the face that they don't like. The players can choose any guard they've met. There is a small ledger where the citizens can write their names and become a guard. The guards are instructed to say 'If you think you're better than me, then you can prove it by signing the ledger'.
A male half-orc conjurer, a female tiefling monster hunter, and a female elf beast trainer are all locals in the town. Each year they meet for drinks at the fair, before competing in their own special game: Ooze Cruise. Each participant is required to bring an ooze to the event. 3 premade stone towers are erected at the outskirts of the fair. The participants climb some scaffolding to place their ooze at the top. The first ooze to eat their way to the bottom of the tower wins. Over the past few years, this selfmade competition has attracted the attention of the townsfolk who enjoy betting on the competition.
Underwater Wrestling. Contestants meet in a large glass tank. They both have to wrestle underwater. The first to surface loses. Some towns use a giant octopus as a champion for an added twist. (Strength/Dexterity Check)
Test your might booth; Challengers are tasked to lift an impossibly heavy rock for 1G, if you can the prize is 50g. (Strength Check)
Midsommar Maypole: Here, drink this. Bad things start happening.
Filthy-Filch'N: The local Thieves Guild branch's secret booth. The local constabulary have had items reverse pick pocketed into their pouches. Bring them all back for a prize! (Sleight of Hand Check)
Greased Pole Climbing contest - there's a tree trunk liberally coated in grease and the first person to reach the top is the winner. Everyone tries to climb at the same time. (Athletics Check)
Gnome Tossing contest - a gnome suitable dressed in padding and helmet can be tossed. The aim is to toss the gnome furthest or to a target. Various bonuses or penalties could be applied to the thrower. Does the gnome co-operate or not ? There are rules in some other subreddits on gnome tossing.
Mimic Or Money. 10gp per game. Players are sat in front of 3 chests and are told to choose one to open. Upon choosing one, the gamemaster will reveal one mimic and ask if they would like to change their answer to the other chest. If the player chooses correctly, they get what they bet plus 10. Upon choosing incorrectly, players have to fight a mimic, the battle lasts until the mimic dies or the player gets defeated, however, the player shouldn't die.
The Cheese Race: Out run the old cheeses rolling down the hill.
A Freak Show. Come see some of the most gruesome sights in the realms! (It's all illusion spells, don't worry!)