Famous Adventures of Jack discussion guide

Author: Berlie Doherty

Illustrator: Steven Wood

Publisher: Cat Nip Publishing

Suggested age group: Year  4 or 5

Synopsis and reasons for selection

‘Which Jack did you want?’
the old lady asked.
‘They’re ten a penny, Jacks are…’

Old Feller Storyteller sends Jill on a magical, thrilling adventure in search of Jack. She enters a world of magicians who can turn into horses, evil kings, dragons, floating castles, beautiful princesses and the most gruesome, fearsome giant of all time, Galligantus. On her travels, she finds brave Jacks, cowardly, spineless Jacks, foolish Jacks, clever Jacks and ‘waste-of-a-wishbone’ Jacks. Jill finds herself in a story of her own, eventually climbing into the swirling, green of a beanstalk…

This collection of short stories, woven together with humour and wit, brings together several famous folk and fairy tales, many set in Cornwall. The language is deceptively simple, but sparkles with magic and emotion. Old stories are given a new lease of life and children will enjoy exploring the clever connections between each tale. Indeed, children who are ready to tackle longer books will be charmed and mesmerised by the amusing, unusual characters, exciting tales and touched by the ending, as Jill continues her own adventure into the unknown...

About the author

Berlie Doherty was born on 6th November 1943 in Knotty Ash, Liverpool and is an English novelist, poet, playwright and screenwriter. She is best known for her children's books, for which she has twice won the Carnegie Medal for ‘Granny was a Buffer Girl’ and ‘Dear Nobody’. Other books include ‘Street Child’ and ‘Children of Winter’. Have the children heard of, or read, any of these stories?

Discussion Points

Before Reading

Using the front cover, ask the children to make a list of what they see, on whiteboards.

Ask the children:

  • What genre of book do you think this story belongs to?
  • What do you think the story might be about?
  • Do you know any fairy tales involving a character called Jack?
  • What usually happens in a fairy tale?
  • Do you know any other fairy stories?

First Encounters

Allow some time for the children to explore the book up to page 12. You can use a paperclip to secure the pages so the children don’t read past this page. If it is possible for the children to have their own copy, they can read at their own pace and write down their responses.

  • Is there anything that puzzles them about the book?
  • Do they have any questions?

Use the children’s questions to initiate a discussion – they will be more engaged if it is something they are genuinely interested in. Some questions might be answered easily, whilst others may need to be investigated at a later date or after further exploration of the book.

Returning to the text

At all stages, invite the children to share their ideas and responses. Avoid asking too many leading or closed questions. The prompts below are simply intended to be used as supplementary questions. Please select or adapt the questions which you think are most appropriate for the children you are working with. They will ask and answer many of their own questions if they are encouraged to discuss their ideas.

Chapter 1: A Tale Begins…

Looking questions

  • At the beginning of the story, where is the girl walking?
  • Where was the black and white cat curled up?
  • What did the fish skeleton turn into?

Clue questions

  • Who do you think the girl is?
  • What impression do you get of the old woman? Explain your ideas.
  • Do you think the old lady likes telling stories? Why?
Thinking questions
  • Do you know any other fairy stories with an old lady, mysterious man and a boy called Jack?
  • Does the first chapter make you want to read on? Explain your ideas.
  • How is the beginning of this story similar to other fairy tales? How is it different?


Chapter 2: The King of the Herrings

Looking questions

  • Ask the children to create a story map of this chapter, showing the events in order. Are they able to add in key vocabulary too?

Clue questions

  • How do you think the horse felt towards Jack at the end of the story?
  • Why did the cat snarl and growl when Jill read out the strange words engraved on the belt?

Thinking questions

  • What do you think the moral of this story is? Why?
  • Jack should never have picked up the feather in the first place. Do you agree?

Chapter 3: Daft Jack

Looking questions

  • How did Daft Jack earn a wage at the beginning of the story?
  • What type of bird took the corn and flew away in the cat’s story?
  • What colour was the handkerchief that Mother Greenwood used to wrap up the bread and cheese?

Clue questions

  • How does Jack feel when he receives his wages?
  • Look at page 32. Can you find any words or phrases that suggest Jack is excited about eating the cream cheese?
  • In the story, the cat runs away never to be seen again. Is there anything interesting about this?
  • What is it about the cat’s story that makes Jill fall asleep?
  • Which word on page 45 tells you that Jill is out of breath?

Thinking questions

  • Money and wealth is more important than laughter and happiness Do you agree?

Personal response

  • Which part of this chapter do you like the best and why?

Chapter 4: The Magic Castle and the Apples of Immortality

Looking questions

  • What was the tree that grew the apples of immortality guarded by?
  • Find a word on page 51 that means the same as ‘weak’ or ‘old’.
  • How did Jack travel across the lake?
  • Can you create your own quiz about this chapter for your class?

Clue questions

  • Ask the children to use a thought bubble shaped post-it to record Jack’s thoughts and feelings on page 50 as he tries to sleep through the night.
  • What image is the author trying to create with the phrase ‘held in the water’s reflection like a still, shimmering fish’? What do you think this phrase means?

Thinking questions

  • Why do you think the author chose to interrupt the story (just as it reaches an exciting part) on page 55 with Mother Greenwood checking the route? What effect does it have on the reader?
  • Are the events on page 60 and 62 similar to any other stories you know?
  • The moral of Mother Greenwood’s story in this chapter is: ‘If you love someone, let them go.’ Discuss

Chapter 5: Jack and the Golden Snuff Box

Vocabulary Journal

Identify a set of target words for teaching. Suggestions are given below, but chose those most appropriate for your class or group.

Get the children to read through the list of words with their partner. Find each of the words or phrases in this chapter. Write down the sentence in the story in which each word appears.

Discuss in pairs what they think each word means.

Share their ideas, directing attention to where they may have heard or seen the words before.

Next, they use a dictionary to check ideas, then write down a definition. Use more than one dictionary to check for nuances of meaning

Reread the text and decide which meanings make the best sense to the story. Finally ask them to write their own sentence

Best printed in landscape. 

 New word

Sentence in story

What I think it means

Looks like or sounds like

Dictionary definitions

My own sentence

hankering (p.78)






insolent (p.80)






ferreted (p.84)






pandemonium (p.85)






Clue questions

  • What do you think the author is trying to suggest about traditional fairy tales in this passage on page 79:

‘And was she beautiful?’ Jill interrupted.

The cat sighed. ‘Of course she was. It’s a story isn’t it?’

  • Who do you think the ‘three nifty men’ might be? Could they have appeared in any other of the stories so far?
  • Can you find any clues on page 87 to suggest that the cat really is scared?
  • Is there any evidence towards the end of this chapter that suggests that Mother Greenwood might be softening towards Jill and becoming a kinder, gentler person?


Chapter 6: Jack the Giant-Killer

Looking questions

  • What did the clever conjuror turn the knights and ladies into?
  • How did Jack kill Thunderdell?

Clue questions

  • Ask the children to place a though-shaped post-it note on page 105 to describe what the duke’s daughter might be thinking and feeling as she is snatched away.
  • Ask the children to place a though-shaped post-it note on page 108 to describe what Jack might be thinking and feeling as he is carried through the courtyard by the giant.
  • Why do you think Mother Greenwood strokes the belt ‘lovingly’ on page 126?

Thinking questions

What effect does the repetition of ‘Run! Hide!’ have?

Does this chapter have any similarities to any other stories you know? (Think about the giant’s courtyard full of humans who have been transformed into stones, slimy trees and begging animals)

What do you think will happen to Jill next?

Who is the main character in this story? Jack or Jill?

The author is attacking the idea in traditional tales that girls are always helpless and saved by boys. Do you agree?.

After Reading – Themes and Cross-curricular links

Jack and Jill’s next adventure

Ask the children to plan and write a new adventure for Jack and Jill. Can they follow the structure of an adventure story, including an engaging opening, a range of increasingly exciting problems, a climax and a resolution, perhaps with a twist at the end? You could challenge them by asking them to refer to other traditional tales.

Alternatively, you could encourage the children to write an autobiography, telling the life story of either the cat or Mother Greenwood.


Ask the children to use maps, books and the internet to research some of the places mentioned in the stories, including St. Michael’s Mount. They could create their own travel brochure, using publishing software, persuading people to visit Cornwall and explore some of the famous beauty spots there.

Freeze frame and drama

Ask the children to choose their favourite chapter. The exciting stories provide an excellent basis for dramatic improvisation and theatre. Can they create a piece to perform to an audience? They could include:

  • mime and movement
  • freeze frames
  • music and sound effects
  • words and phrases taken from the story

Plants and Seeds

Encourage the children to find out about different types of seed dispersal. Provide the children with pictures of poppies, acorns, coconuts and sycamores. How is each seed dispersed?

Give the children beans and ask them to investigate how they will grow in different conditions – in the dark, too little water, too much water etc. What do the beans need to grow? Ask the children to plant their beans in transparent cups, with compost. Allow the children time over the next week to use a diary to make observations, notes and diagrams and measure their bean as it grows.

Twisted Tales

The book wonderfully subverts this well-known genre and plays on children’s familiarity with traditional tales. Children may also enjoy reading The Sleeper and the Spindle by Neil Gaiman, The True Story of the Three Little Pigs’and The Frog Prince Continued’ by Jon Scieszka, The Three Little Pigs by David Wiesner and Jack and the Baked Beanstalk by Colin Stimpson.


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