Interactive Carnival Games

Hey! I am trying to write the next session of my campaign, which has a political medieval theme, and the characters are going into a town which will have a carnival happening. For this, I've been researching both normal carnival games and violent games played throughout history. I have ideas for the more violent games, but as far as regular games have gone, I've only found things along the lines of tic-tac-toe and other stuff like that. The problem with this is that I want these games to be very interactive, and for games like that it would pretty much be me telling the players to role an intelligence check a few times. In my friend's campaign, there was a festival and the games were rolling based, but also included things like rapping and speed-rolling, which all of us found very fun. Let me know if you have any ideas for games and how I could make them more interactive!

Gambling is always a solid option because got don't have to worry about how to run it using the rules of dnd-- you just run a game within the game. 

My go-to gambling game is a simplified version of 21 with d10's. Each player puts down a certain amount of gold per hand and rolls 2d10's to represent your first two cards, and to "hit" you just roll an additional d10 each round until you think you've gotten as close as you can to 21 without going over. 

The beauty part is it's relatively simple so you're not wasting game time explaining it (especially if the rogue should already be an expert on this kinda thing) but it's got enough risk/skill factor to still be interesting. 

Somebody asked a similar question a while back or so, so if it's okay I'm just gonna copypasta the responses I gave them....

The Lobster Race:  A relay race with two teams of four runners each who each run a 90' leg (like around a baseball diamond). But instead of carrying and passing a simple baton, the runners have to carry and pass a live lobster! It's just a bunch of Athletics checks really. Each runner rolls athletics, lower roll goes their movement speed, higher roll goes their movement speed + 5 feet. But each time they roll athletics they also roll a d6. If they roll a 1, that runner gets bit by their lobster, causing them to move only half their movement for that roll. Just tally the distance each team goes until one team reaches 360 feet. 

The Ring Toss:  For one copper piece you can try to throw three rings onto the upright fishing poles standing 15 feet behind the counter. It's just three Dexterity checks, but the DC keeps going up because at first the poles are stationary, but once you start throwing the rings and hitting the poles, the poles start flexing and swaying. So the 1st roll is DC 15,  2nd roll is DC 20,  3rd roll is DC 25. Two successes wins a small prize, three successes wins a bigger prize. 

Fish in a Barrel:  This is basically cornhole but with live fish. There are two sets of barrels filled with water and fish set 20 feet apart. Each contestant must reach into their barrel, grab a live fish, and throw it into the barrel 20 feet away. Just set a timer for 30 seconds and have the two players roll Dexterity checks as fast as they can. Whoever beats the most DC 20 rolls in those 30 seconds is the winner. 

The Fool's Joust:  Imagine a simple split rail or rope fence marking off a 25 foot diameter piece of ground. The contest is between two teams of two players each. On each team, one person sits on the other person's shoulders. The person on bottom (the Mount) is then blindfolded. The person on top (the Striker) is handed a pugil stick (a 5 foot long thick staff with a padded leather ball at each end). The objective is to knock the opposing Striker off their Mount. When the bell rings, each Mount makes an Athletics check. Whoever rolls higher, their Striker gets to attack first, making one attack roll (using Strength, Proficiency is at your discretion). Then the other Striker gets to make one strike, but at disadvantage. The Armor Class they're aiming for is 10 + the higher Dex modifier of the two opposing players. Whichever team scores 3 hits first wins. If you really sell it with the descriptions of the hits and misses it'll be hilarious. My players loved it. 

Oh, and of course the people in the crowd bet on the outcome. So the players who are watching might win or lose some money based on how well their friends do.