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Sponsored By:

westport library
meryl moss media
westport-center-for-senior-activities
booktrib

“Dear Jackie Robinson,” …

Enter the Jackie Robinson Intergenerational Letter-Writing Contest!

Jackie Robinson didn’t just break baseball’s color barrier — he broke barriers in hearts and minds, paving the way for generations to dream bigger, stand taller and speak louder. Now, you can do something to honor his legacy — a heartfelt letter addressed to Jackie Robinson.

With the intergeneration connection in mind, we highly encourage submissions from teams of two — ideally, one senior (60+) and one young person (ages 6–21).

We also welcome individual responses or teams of two of any age.

Writing Prompt

Compose a letter to Jackie Robinson, expressing how his life, achievements and legacy have personally impacted you.

If you are writing as a team, you can write from both of your perspectives or tell one shared story that weaves your voices together.

Submissions must be typewritten and no more than 800 words.

Important Dates

  • Submissions Open: February 11
  • Deadline to Enter: March 15
  • Winners Announced: April 15 (Jackie Robinson Day 2026)

Awards and Judging Criteria

We will award one grand prize winner and two runners-up.

Entries will be judged on the following criteria:

  1. Emotional impact and authenticity
  2. Clarity and quality of writing
  3. Connection to Jackie Robinson’s legacy
  4. Representation of intergenerational collaboration (if applicable)

SUBMIT YOUR LETTER HERE

This year’s contest submissions have closed!