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February is the month of love—but not all love stories are the same. This month, we challenge you to put your literary wit to the test with two bite-sized contests inspired by classic literature. Join in our cross-over contest for both New Canaan & Greenwich.


For ages 15 & Under: “Love Letters from Storybook Characters”
The winner receives $25 and publication in the Sentinel!


Prompt: Ever wonder what Cinderella’s glass slipper might write to her foot? Or what the Big Bad Wolf’s love note to Little Red Riding Hood would say? In 50 words or fewer, write a Valentine’s message from one famous storybook character to another—whether romantic, funny, or just plain weird!


EXAMPLES:
Dear Humpty Dumpty,
You may have had a great fall,
But to me, you’re the greatest of all!
Cracked or whole, you’re still my friend—
Little Miss Muffet

Dear Puss in Boots,
I like your hat. I like your boots. I like the way you trick people with big words. If I had nine lives, I’d spend them all going on adventures with you. Your fan, Jack (from the Beanstalk)

For ages 16 & Up: “Shakespeare in Six or Twelve Words”
Winners receive $100 and $50 and publication!


Prompt: The Bard was a master of love, tragedy, and mischief—now it’s your turn. Summarize any Shakespearean love story in just six or twelve words – your choice.

Whether it’s “Much Ado: Enemies, rumors, wedding, still single”; Hamlet: “Dad’s ghost returns. Bad idea, everyone”;  or Macbeth: “Witches whisper fate, Daggers gleam, guilt stains his hands— All is lost.”

Make it clever, poetic, or laugh-out-loud funny!


Deadline: Friday, February 28, 2025. Winners announced in the March 7, 2025 issue.

How to Enter: Craft your clever response to this month’s prompt, then enter it below.

Multiple entries are welcome, and pseudonyms are accepted—giving you the freedom to be as inventive as you like.

A classic contest finds a home in New Canaan, inviting wordplay enthusiasts and literary artists to have fun, showcase their creativity, and win a cash prizes each week.
  • Type your name as you wish it to appear in the newspaper should your entry be chosen. (required)
  • This will not be published. (required)
  • This will not be published. We will use it to contact you in the event of questions.
  • Type in the number of the competition for which you are submitting an entry.
  • Either type your entry in this box or use the copy/paste feature from another program.
  • Either type your entry in this box or use the copy/paste feature from another program.

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