I have won this many times, but it seems like some competitions are harder than others to win. You can try bribing the judge, but here are some combinations that seem to work more than others. If you know who the mayor is, become best friends with them BEFORE the Fair. Ideally, arrive at the Finchwick Fair as soon as it starts and place your entry. I suggest doing only 1 entry at a time if you want the aspiration completed. Try not to interact with the Mayor unless you're bribing them. If they don't go around and judge your entry, then you might not get anything. Stay the whole time until after the fair disappears and it gives you the reward close to midnight.
1. Oversized crop competition: Any large crop as long as it's in perfect condition. I've even won with medium and small ones that are perfect quality, but I would choose the largest one you have.
2. Chicken Fair: Evil Chicken, but it has to be a rooster, not a hen. You can sometimes win with a golden rooster, but evil one has a pop up when it ages up that says it's the best for the fair. Maxing your relationship with it won't hurt and make sure to keep the coop clean and the rooster fed so it's a young adult and very happy.
3. Egg Competition: Obsidian or Golden egg in Excellent condition. This one is hard because eggs spoil, but if you put it in your household inventory, that completely stops the timer on it.
4. Wool Competition: Excellent rainbow wool. This may vary though. I've had it not win.
5. Garden Competition: Perfect quality death flower.
6. Pie Competition: Cannot get anything to win no matter what even with a cow plant essence pie. Bribe the judge and have good charisma, mischief and debate maybe? Be in a very confident mood.
7. Llama competition: Very happy, young adult llama with max relationship to the sim submitting the competition. Feeding it a rainbow treat might help. This one is a toss up and doesn't always work.
8. Cow competition: Very happy, young adult cow with max relationship to the sim submitting the competition. Feeding it a rainbow treat might help. This one is also a toss up.
9. Milk: I'm guessing excellent rainbow milk, but I haven't tried this yet.
