After Ness and Paula are trapped, Paula sends a message to Jeff in Winters.
Jeff wakes up after hearing Paula's psychic message, which asks him to go south.
Get the Bad Key Machine from Maxwell
Try to exit the room. Tony will leap out of bed to ask you where you are going. Tony says to go to the locker room to pick up some supplies for the journey, and then he will join you. Exit the room.
If you talk to the boys outside of your room, you will learn about Tessie, Cave Boys, and Stonehenge. The other room has a bunch of cookies, but don't get them yet.
Go downstairs, then go into the first room. Talk to Maxwell to hear about Jeff's father, Dr. Andonuts. Maxwell will give you a locker key, but he warns that it is bent. Go into the locker room next door and try to use the key on a locker. The key is too bent to work. Talk to Maxwell, who quickly invented a Bad Key Machine just now.
Get Equipped, and Leave the Boarding School
Use the Bad Key Machine to open all of the lockers. Equip the things that you find here. If you didn't get any of the cookies from the room upstairs, get them now. Jeff has a Ruler and Protractor, but these items don't actually do anything, so you can drop them to make room for the rest of the cookies if you wish. But you will need one free space in your inventory soon.
Now you are ready to leave the Snow Wood Boarding School. Go outside and talk to Tony to climb over the gate.
Befriend Bubble Monkey
Go east and enter the drug store. Talk to the woman next to the counter. Buy a pak of bubble gum from her and then talk to the monkey, who will join you after taking some gum. If you use the phone, you can call Maxwell to save the game.
Talk to the Tessie Watchers and Stay Overnight
Go south from the drug store, then when you can't go farther south, go west. Then go south at the end, then east. Go can go into the tent and talk to the boys to heal your HP.
Go west from there, then south, then east. You find a camp site of Tessie watchers. You can heal up in the tent on the left. While sleeping, Jeff might repair the broken item(s) that you have with you. Also, you might hear messages from Paula.
Hitch a Ride with Tessie
If you haven't rested in the tent on the left, do so to continue. When you exit the tent, it will be windy outside. Go east along the shore. If you walk in front of the tent near the strip of land that sticks out into the water, the Photo Man will come down and take your picture.
Go to that narrow strip of land and walk onto the circle of dirt at the end. The Bubble Monkey will chew some gum and float over the water, and Tessie will emerge. She will carry you and Bubble Monkey to a distant shore.
Go through Brick Road's Maze
Follow the path and you will discover a cave entrance and a pencil statue. In the cave, there is a small maze. There are a few monsters and gifts inside. The north path goes to a Bread Roll. The middle path goes to an Insecticide Spray. The lower path leads to a split, where you can go to the right to get a Broken Iron, which Jeff can turn into a Slime Generator if his IQ is at least 10. The Slime Generator temporarily immobilizes enemies when used in battle.
After getting the Broken Iron, go back to the split in the path, and go west. When the path splits again, go north. You can check on the sign to the north to have your picture taken by the Photo Man. Then go southwest until the path splits, and go west until you reach another split. Go south there to get a Croissant. Then go northwest until the path splits again. Go west and south to get a Stun Gun. Then go back to the split and go southeast. From there, the path is straightforward. You will reach a phone, where you can call Maxwell if you want to save the game.
Exit the maze. Talk to Mr. Brick Road. He will tell you about the maze and will heal your HP.
Get Bubble Monkey's Help through the Cave
Continue on the path, and you will find another cave. Inside, go west and you will find a Hamburger. Go through the door on the left. When you see some ropes, go up the first rope to find a Cheap Bracelet. Then go back down the ropes. Go west to find a Bottle Rocket. Then stand below the coil of rope and use the pak of bubble gum to make Bubble Monkey throw the rope down to you. Climb up. You can't fight the shining thing, so just go west to leave the cave.
Ride the Sky Runner
Go outside to find Stonehenge. Bubble Monkey will leave. Avoid the Cave Boys and go south to find a lab. Inside, you meet Jeff's father, Dr. Andonuts. After some awkward chit-chat, he eventually tells you about the Phase Distorter and the Sky Runner.
After this, you can use the machine in the back to heal up. You can go upstairs to get a Broken Pipe from the gift box. Then go downstairs and go to the left. You will find the Sky Runner. Get in (talk to Dr. Andonuts again if it doesn't let you in) and press a button to make it lift off.