A Clockwork Pelican
The first method of clearing this challenge is by finding the pelican doll in the lobby of the train station. Use its ability to fly up to the nest, which is located close to where the doll itself is found.
When you reach the nest, stack out to Charlie and hop into the manual winder. Jump up and down to wind the clock.

A Gentleman's Solution

For the next method, use Charlie to head into the small opening near the door with all of the gears on it in the lobby.
Have Charlie hop into the door overwide pump and jump up and down to open the door.
Now find the doll in the burgundy suit near the recently opened door and stack into him.
Head through the door and use his firm handshake ability to shake the hand switch, which will manually wind the clock.

Wind Under Your Wings

Stack into a balloon child and then head over to the train that took you to the Zeppelin level. Stack into the engineer with the large blue and white striped hat and head to the area with the small opening near the door that Charlie fit through to complete the previous method.
Use the engineer's ability to blow smoke out of his top, then stack out and use the balloon boy's ability to fly up to the perch above.
Follow the path to the next winder and use Charlie to activate it.