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‘Dear Jackie Robinson’: Second Jackie Robinson Essay Contest Deadline
Contest Details
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 honor his legacy.
The Westport Library, Westport Center for Senior Activities, BookTrib, and Meryl Moss Media are teaming up to present the second Jackie Robinson Essay Contest, geared toward those 60 and over.
This year’s contest is asking the community to come together to write, or co-write, a heartfelt letter addressed to Jackie Robinson. Reflect on how his courage, dignity, and perseverance have impacted your lives and your relationship with each other.
Prizes will be awarded to the top three finishers. Click here to submit your entry.
With the intergeneration connection in mind, we highly encourage submissions to be teams of two — ideally, one senior (60+) and one younger person (ages 6–21). We also welcome individual responses or teams of two of any age.
This is more than a writing contest — it’s a chance to build connection across generations, celebrate social progress, and share powerful stories.
Why Enter?
Because this isn’t just about writing — it’s about sharing stories that deserve to be told. It’s about grandparents and grandchildren, mentors and mentees, neighbors and friends finding common ground through a legend who changed the world.
Come together. Write with purpose. Celebrate a hero.
How To Enter
Compose a letter to Jackie Robinson, expressing how his life, achievements, and legacy have personally impacted you. Make it genuine, thoughtful, and no more than 800 words.
Who Can Enter
- Anyone and everyone (seniors and duos encouraged)
- One senior (age 60+) and one young person (ages 6-21)
- One senior (60+) and a friend, neighbor, or family member — any duo with a meaningful connection
- Individuals submitting as a single entry
Prizes and Recognition
We will recognize one grand prize winner and two runners-up, and maybe more!
Important Dates
- Deadline to Enter: March 15
- Winners Announced: April 15 (Jackie Robinson Day 2026)
Submission Guidelines
- Letters must be typed and no more than 800 words.
- Submit as a PDF or Word document by submitting through this form.
- Include:
- Names, ages, and photos of participant/s
- Relationship between participants (if applicable)
- Contact email and phone number
- Title of your letter
Judging Criteria
- Emotional impact and authenticity
- Clarity and quality of writing
- Connection to Jackie Robinson’s legacy
- Representation of intergenerational collaboration
Sponsors
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The Westport Library is committed to intellectual freedom, inclusivity, and lifelong learning. Our mission is to provide welcoming spaces for the free exchange of ideas. The Library does not endorse or condemn points of view, including any program content or the views expressed by presenters or participants.
