.. Climb up the hole

Some kind of rope would help.

Have you read any interesting books, lately?

Like a book about party tricks?

There is a party trick book in the basement bookshelf. Take it. And read it.

But one trick is particulary interesting.

Pulling handkerchiefs out of a hat.

You just need a hat. ( There is the witch's hat in the upstairs hallway. )

Great! Do the trick then.

Use the trick book on the hat. You get a handkerchief chain!

You can use it to climb up the hole.

Attach something heavy to it, first. ( There is a paperweight in the right drawer downstairs. )

Attach the paperweight into the chain and use it on the roof hole.