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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