Crawl forward and keep going until you get to the roundabout, which is of course stuck in place. To the right of the roundabout is stone in the shape of an owl, take it and the roundabout will move.
Proceed crawling forward and you'll eventually find the second memory way across the otherside. When you see the memory, take a right and keep going down the tunnel and into the playground.
Immediately after sliding down, you'll find another owl stone and a seesaw right in front of it. Take the owl and interact with the catapult to find that you need more owls in order to use it.
Crawl down the hill, towards the left side and keep going until you see a small shed that's open. Enter the shed and grab the third owl.
Exit the shed and you'll see that the fence to the playground is now open. Go through the door and turn left, you'll see some pebbles on the side of the road, follow them.
As you walk on that path you'll find another roundabout that's stuck in place. Look to your right and you'll see some stones, start climbing up on them and drop down on the opposite end.
Around the corner of the roundabout is another owl stone, which makes for 4 pieces now. Head back to the center of the playground.
When you get back to the playground, you'll find some shoe prints on the ground. Follow them into the fenced area and drag the smaller box out of the way to reveal a hole behind the fence.
The area is dark, so hug onto Teddy and proceed forward into the secluded area and turn right. You'll find a tunnel there, drop down on it.
Follow the narrow path and you'll eventually find a pit fall. You can either lean a little forward and grab the owl from the otherside or go around and walk on the plank to get to the owl safely.
After taking the owl follow the path on the right side and keep going until you see the exit. Remove the piece of wood that's locking the door. Exit the tunnel and turn right to get back to the playground.
Once you get back to the entrance of the playground, turn right and you should see another path right between the fenced area and the first path you took. Take that path and you'll see a chest that's held shut by a rock.
The rock is too heavy for you to lift, so climb up on the tree stump to the right side of the chest.
Look up and you'll see a tire that's hanging from a tree branch. Drag the tire out of the tree and it will hit the rock, causing it to fall off of the chest.
Place all 6 owls in place and climb up on the otherside of the see-saw and climb onto the platforms at the right side of the seesaw.
Make your way around the tower until you get to the top, then head for the bridge and keep walking towards the black and white area on the otherside.
Crawl through the path and take the musicbox from the memory of your mother, then proceed through the path behind her.
Get into the tunnel at the end of the bridge and you'll find another pipe that you can climb down on. Climb through it to get back to the playhouse.
Once you're back, place the musicbox inside the machine again and crank the valve until the machine places the musicbox in one of the tubes by the door.
Teddy will automatically open the door for you this time. Head through the door and drop down the tunnel again to get to the next area.