25 Festival Events and Contests for 5e

Grab your spare change and get ready for some downtime! Every so often, even adventurer’s need to blow off a bit of steam! 25 Festival Contests and Events is a companion to the Holidays, Festivals, & Celebrations RPG Blog Carnival.

Edit: This article has been updated for May 2021 RPG Blog Carnival hosted by: Full Moon Storytelling. Thank you for hosting!

Winning contest should yield amazing prizes! This can come in the form of some spare spending money, wonderous magical items, weird potions, or tickets that can be exchanged for prizes. Magic items won this way should not be the most powerful, granting stat bonuses, or amazing powers, but instead should have weird and only potentially useful effects. For inspiration, check out our Magic Item Name Generator.


Sit back and enjoy all that the festival has to offer! Some entertainment can even be entered!

  1. Comedy Act – Be prepared to sit back and chuckle hard as a comedians take the stage. I hope you’re ready for some audience participation.
  2. Short Play – Actors and Actresses take the stage, end entertain you with tales of love, life, and daring heroes.
  3. Parade – Truly a wonder to behold, each town has a different form of parades, that is sure to please the crowd! Want to participate? You can enter when you succeed on a performance check (DC15)
  4. Concert – Minstrels and Musicians come from far and wide to Brightest Day. Relax and enjoy! You can enter when you succeed on a performance check (DC15)
  5. Group Dancing – Line dancing, Square dancing, or Court dancing, anything goes!
  6. Face-Painting – It’s not only for the children!
  7. Ale/Wine Tasting – Spirits guaranteed to lift your spirit!
  8. Pie Tasting – Who wouldn’t be up for some pie tasting? Usually following the cooking contests, tastings are pretty common! Who doesn’t love free food? Want to enter your pie? Roll Survival! Third place is DC 15, second is DC 18, and to take the grand prize DC 21.
  9. Dunk Tanks – Usually only present in the bigger cities, but a fan-favorite for sure! You too can dunk someone when you succeed on an athletics check (DC 13).


3-Legged Race

Any Number of Participants, in Pairs
A teamed race across 50 feet, where one of each of their legs is tied together. The first team across first is the winner!
Each participant will roll Athletics or Acrobatics with Disadvantage, and add it to their partner’s score. You move in feet equal to this combined score -10. If this total is below 0, then the partners fall over, moving backward.

Archery Contest

Any Number of Participants
50 feet out, with only 3 Arrows in hand. Who can get closest to the Bullseye?
Each participant makes 3 ranged attacks with Advantage to hit the target. Each of these rolls will be added together to get the final score.

Arm-Wrestling Contest

Even Number of Participants, 10 or less, 1v1 Elimination
Two opponents square off against each other in the ultimate show of strength, pushing each other’s arm’s over. This is a one vs one elimination game until the true master of muscle remains!
Each Round, the Participants, and their opponents can roll one of the following:
1) Athletics Check
2) STR Check
If one Participant’s result is 5 or more over their opponents, they win the match! Matches continue until one Participant remains.

Barrel Run

Any Number of Participants.
Each participant will try to run on top of a barrel for a length of 50 feet. First across is the winner!
Each round Participants will roll Athletics. When 2 contestants are at the same amount of feet, either contestant can decide that their barrels collide. When this happens, both participants must roll with Disadvantage on the next round.
Result 7 or under: You become unstable, you do not move during this round. If you are already unstable, you fall off your barrel and are removed from the race!
Result: 8+: You move forward in feet equal to the result -5.
When 2 contestants are at the same amount of feet: Their barrels collide.

Bobbing for Apples

Any Number of Participants.
A Time Honored Tradition! You try to grab 5 Apples from the barrel as fast as possible.
Each round Participants will roll acrobatics (DC 10). Each time a participant succeeds, they grab an apple. The one with the lowest number of rolls is the winner.

Fishing Contest

Any Number of Participants
Two contests in one! This measures the Number of Fish caught and the Biggest Fish.
Each Participant can take 5 actions. Each action they can choose to:
1) Roll a WIS Check
2) Roll a Survival Check
3) Roll a WIS Check with Disadvantage + Survival Check with Disadvantage
The person with the highest single roll is declared the winner of the Biggest Fish award, and the highest total score gets the Most Fish Award.

Horse Racing Contest

Any Number of Participants
A Horse Race through the streets of the city!
Each Participant can take 5 actions. Each action they can choose to:
1) Roll a DEX Check
2) Roll an Animal Handling Check
3) Roll a DEX Check with Disadvantage + Animal Handling Check with Disadvantage
The highest score is the fastest participant!

Karaoke Contest

Any Number of Participants
Single-handedly the most heated contest of any festival! Contestant perform in front of a crowd, where the Applause-o-meter goes off the charts!
Each Contestant must choose a song by rolling an Insight Check with Disadvantage. Then they will roll 2 Performance Checks for the song they are singing. These rolls are added together to determine the total score, and prizes are given accordingly! If two are tied for First, then a “Sing-Off” will happen. The two remaining will roll Performance Checks in succession until one participant’s roll is higher than their opponents twice in a row.

Log Rolling Contest

Even Number of Participants, 10 or less, 1v1 Elimination
Trying to balance on a log is hard, trying to balance on a floating log while someone is trying to knock you off, nearly impossible!
Each Round, the Participants, and their opponents can roll one of the following:
1) Athletics Check
2) Acrobatics Check
3) Athletics Check with Disadvantage + Acrobatics Check with Disadvantage
If one Participant’s result is 5 or more over their opponents, they win the match! Matches continue until one Participant remains.

Magic Trick Contest

Any Number of Participants
A show of magic, wonder, and ancient secrets! This is where Wizards, Witches and Sorcerers shine!
Contestants will choose 2 cantrips to be shown as a display of magic and roll for them. Sleight of Hand can be used in place of a cantrip, but you will have to roll it with disadvantage. The participant will roll a Performance Check. These results will be added together for the contestant’s total score.

Musical Chairs

6-10 Participants
A childhood favorite, that turns brutal with age. Participants will walk around a circle of chairs, of which there are one less than the number of participants, as music plays. When the music stops, each participant must struggle to get into a chair to not be the one remaining standing, who is removed from the competition. This continues until one participant remains.
Each round, participants will each roll an Acrobatics Check, then an Athletics Check with Disadvantage, and add these results together. The participant with the lowest total will be removed, and the next round starts. In the event of a tie, the participant with the highest Athletics Check will be the winner. If this too is a tie, then the participants roll opposed Athletics checks.

Pie-Eating Contest

Any Number of Participants
Who can eat these pies the fastest? Simple, fun and delicious!
The Pie Eating contest is done in 3 rounds, each increasing in difficulty (DC 10, DC 14, DC 18). Each round, the contestants will have their choice to take one of the following actions.
1) Roll CON check with disadvantage to eat as fast as possible. This will take 6 seconds.
2) Roll CON to eat at a fast pace. This will take 10 seconds.
3) Roll CON with Advantage to eat at a normal pace. This will take 14 seconds.
If at the end of a round, the contestant fails the DC, they choke and lose 10 additional seconds. At the end of 3 rounds, whoever has the lowest seconds is the winner!

Storytelling Contest

Any Number of Participants
The audience waits on bated breath for you to finish your narrative! How can you turn a boring story into an epic tale? 
The Dungeon Master will order the subjects Arcana, History, Religion, and Nature into any order; one of the four being the crowd favorite, and one being the crowd’s least favorite. Each Participant can either choose one of the subjects at random or roll an Insight Check (DC 18) to determine the crowd favorite.
Each Participant will then roll a Skill Check with their chosen Subject. If it is the favorite, they will have advantage on this roll. If they roll the least-favorite, they will have disadvantage on this roll. The other two subjects are rolled as normal. The participants will then roll a Performance Check. Each Participant has their Performance and subject results added together to determine the champion!

Tree Stump Chopping Contest

Any Number of Participants
Let’s clean up this town. Chopping up a tree stump can definitely draw a crowd! The first to chop across the stump is the winner! This stump has AC 10, and 40 HP
Each Participant will get a chopping axe worth 1d4 Damage. Each participant will make attacks with the chopping axe each round. However, for each 5 your attack is over the AC, roll an additional die of damage. Whoever can reduce the stump to 0 first is the winner!


3-6 Participants per Team
This is a teamed sport! Each team will pull on one end of a Rope, trying to pull the other team into a puddle of mud!
Each team will roll Athletics twice and add all of their checks together. The team with the highest score will become the ultimate champion and get the Tug-Of-War Award.