Firstly, run down Main Street (to the right) until you reach the Pumpkin Patch where you’ll meet Linus and Lucy. Linus will request you to help him find the heaviest pumpkin in the pumpkin patch. Since you will be timed by Lucy, the fastest way is to put two pumpkins on the weighing scale and take away the lighter one. Once you’re done, drag the heavier one to Lucy. Then Lucy will ask you to push the pumpkin back to their house. This starts a difficult mini-game where you have to push a pumpkin along hills and through obstacles.
There are many places where the pumpkin may fall off or get hit by something and be damaged. If it breaks, you will get sent back to either the very beginning or the last checkpoint. There is one part where you need to push the pumpkin through the log which is easy, so just push it really hard till it rolls through. The toughest part is close to the end, where there are three kids on swings. The best way to tackle this is to position the pumpkin right next to the first swinger and then as soon as she passes you while swinging backwards, run and push as fast as you can all the way through. If you do it properly, you will be able to get the pumpkin to Lucy.