Pickles very important. Not sure why.
Carnival of Tears has exactly what you're looking for. Basically just pick a carny game from modern times, assign it whatever skill check you think it takes to play that game, and describe it as being made of wood and gears.
Outside of gaming, all my knowledge is for Renaissance Faires, not medieval ones. So I'm not sure if giant turkey legs are appropriate to have.
Otherwise, anything a group of drunk/happy people can do for pretty cheap with what they have on hand and in the local terrain.
Two words: Pig Wrasslin'.
A time-tested pastime that's given joy to generations of folk.
A fair was generally a market in reality. The regular gathering of traders and entertainers which descended on a town holding the appropriate charter.
The main purpose is therefore to sell things, think of walking down a local market street in the Middle East or Far East for the atmosphere. Throw in entertainers like fire-eaters, dancing dogs and bears, exotic creatures such as monkeys and big snakes, and plenty of less salubrious entertainment on offer.
Contests would be small if present at all. Maybe wrestling on a greased pole, catching a greased pig or throwing horse-shoes.
Larger contests, such as archery competitions and the like, are more at home in a festival or tourney. Plenty of games and activities were there for the common folk as well as the more famous jousts and mock-battles between the martial classes. A festival would often also include a parade with plenty of pangeantry from the local guilds.
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How big or involved do you want the event to be? Is there a theme? Is there a point you want to make with the event?
I recently homebrewed a version of the English Barrel Festival. Basically in my homebrew town every year they celebrate brewing and the woods all in one at this fair. It starts with a blessing, then there's lots of endurance games, drinking contests and tests of ranged skill. As dusk gives way to nighttime the barrels of pitch lining the streets are lit on fire and marched out to a field or meadow which is then ritually lit on fire (controlled by magic) and more games are had until a final blessing ends their agricultural year (this fest is held in late autumn).
The games were:
Archery
Axe throwing
Speed drinking
Marathon drinking
Keg stands
Mug Juggling
Trivia contests (telling herbs by smell, identifying brews by taste, etc)
Rail slides
Wrestling
Pig Wrestling
Spar tossing
Hammer throwing
Feats of strength (hoisting barrels, logs, bending hoops, etc)
There were others that I know I'm forgetting but this gives you the basics. Since the whole thing is put on by common folks and the churches there's not a lot of money in it; most of that goes to food and drink which is all free for the duration of the Barrel Festival. So instead contests were played for more modest prizes. Since I have the Ultimate Campaign book and use the Downtime system, I awarded Capital for prizes.
Some games were for bragging rights (Influence), others for minor tools or supplies donated by businesses (Goods) and still others gave favor to the winners by the patrons of the game (labor). So for example since the Twin Stag Pub sponsored a number of games they would lend out the strong arms and backs of some of their workers to winners for future endeavors (1-3 points of Labor).
Now since the main event of the fest was the Barrel Run and the subsequent Barrel Throw, those were both major awards. The dwarf PC in the party took part and provided legendary sport.
The Barrel Run was a 6-leg endurance challenge forcing 6 Fort saves. They began at DC 10 but added +2 every leg. Competitors could pass their barrel to another but their run ended at that point. They could also miss one save but keep moving under the Fatigued condition; the second failed save means the competitor is Exhausted, drops their barrel, and has to make a Ref save (DC 15) to avoid burning pitch.
The dwarf PC made 4 saves in a row, faltered, but elected to keep going. He made the 5th and JUST BARELY managed the 6th to be the first competitor in years to complete the whole run. His closest competition only made 4 legs so he was a smashing success. Unfortunately his Fatigued condition caused him to lose the Barrel Toss but he still made 3 Influence out of the deal and for weeks afterwards people were still buying him drinks for the effort.