For this achievement you need to talk to boomer the pig and do his mission of getting him an apple
In my video I show you the best route to take to get all the challenges and achievements within the 5 min speed run
Speak to Charlotte: 1:20
Collect 3 Pumpkins: 1:40
Striped Pumpkin: 1:45
Spookify Scarecrow: 2:45
Boomer's Bidding: 3:10Harvest Crops: 4:05
Peepaw's Hat: 4:50
Achievement walkthrough: