The goal of this stage is to find three Master Emerald shards. This place is a level with a Halloween-like theme. Standby rockets allow the player to travel through the level with ease, though gliding is an simplistic method of navigation as well. There are many pumpkins and ghosts that appear with no warning to surprise the player. King Boom Boo's Boos make their first appearance in this level. G.U.N. robots also appear to attack the player throughout the level, ensuring that the player is not successful in their mission.
An interesting piece of trivia is that this is the only stage to not have a gold beetle at all in the GameCube and HD version. In the original Dreamcast version, it is found just off the ledge with the middle switch on ghost train mountain.
Pumpkin Hill has three major areas:
Pumpkin Mountain: An area dominated by various types of pumpkin and fire-breathing mechanized skulls. There is a Ancient Ruin at the summit that opens up a new area.
Church Mountain: A mountain with a blue and lilac church at the summit. It has many tombstones in front of it, mimicking a cemetery. A dangerous Boo can be found there and it will follow the player in order to inflict damage.
Ghost Train Mountain: A mountain with a turntable directing a Ghost Train. It leads to a Pumpkin Head Mountain with a trail of Ring Balloons.The area features many different trains on top of a hill with many rails and even a turn table.The hill also has a few doors and cages which on of them has Big the Cat in it for unknown reasons.
Level Up Item
Knuckles obtains an Level Up Item in this level; the Shovel Claw. This Level Up Item allows him to dig and is necessary for at least one Emerald Shard requires digging. Further levels also need this Level Up Item.
Find the three pieces of the Master Emerald
This mission is simple as Knuckles has to find the Master Emerald pieces around in Pumpkin Hill. Knuckles will need the Shovel Claw that is in plain sight as a Master Emerald piece will, most likely, be hidden underground. Master Emerald pieces can also be found on the three main mountains or on some of the large pumpkin structures around the outside of the stage.
Collect 100 Rings
This mission is very simple now that Knuckles has the Shovel Claw. Knuckles can simply dig underground to find buried rings. Rings are also scattered around the three mountains and the G.U.N. robots and Boos are limited here. Flying through the ring balloons will also help as well.
Find the lost Chao
As always, Knuckles will need the Mystic Melody in order to proceed through the mission. In fact, Knuckles will only need the Mystic Melody for this simple lost Chao mission. Knuckles will need to take the rocket to Pumpkin Mountain and play the Mystic Melody at the Anicent Shrine there. Afterwards, Knuckles can jump up to a portion of the mountain and get to the lost Chao.
Collect the Emerald pieces in 3 minutes
This one isn't too difficult as, despite it's size, Pumpkin Hill is pretty easy to navigate through if one learns the layout. Knuckles may need to use a hint computer or two if he has trouble finding some Emerald pieces.
Complete Hard Mode
Hard mode requires two Level Up Items: Sunglasses and Shovel Claws. The level has many more Boos including the Boom Boos, larger versions of the regular type, floating around the rockets and tombstones. The shards are in fixed places, the first requiring skill and patience, the second digging and third the Sunglasses, patience, timing and more skill.