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Three Generations. One Marathon. A Shared Purpose

  • Pencils of Promise
  • Uncategorized
  • September 16, 2026

For Madi McSherry, running a marathon was always something she wanted to check off her bucket list. She just didn’t expect it to become a three-generation family adventure, or a way to champion education along the way.

Madi’s marathon journey began with a promise.

Last year, her grandfather told her that if she ran a marathon within the year, he would run it with her. It would be his sixth marathon and, officially, his last. There was just one small complication: he already has a “26.2 x 5” tattoo.

Naturally, Madi said yes.

Soon, her dad and uncle decided to join too. This October, four McSherrys will take on the Bank of America Chicago Marathon together, bringing three generations of their family to the starting line.

But Madi knew she wanted her first marathon to stand for something beyond the finish line.

As a preschool teacher for the past three years, education has always been close to her heart. Early in her career, she worked at a state-funded preschool in New Jersey that provided free education and resources to families in need. That experience showed her firsthand how much access to quality education can shape a child’s life.

So when Madi looked through the charities participating in the Chicago Marathon, Pencils of Promise immediately stood out.

“I knew I wanted to support a charity rooted in giving children access to education,” Madi shared.

She was also drawn to PoP’s commitment to teachers, not only supporting students, but investing in educators through training and innovative resources.

Because for Madi, supporting children also means supporting the people who help them learn, grow and dream.

This October, as Madi and her family run 26.2 miles through Chicago, they’ll be carrying that purpose with them.

Three generations. One marathon. And thousands of children whose futures are being shaped by access to education.

We’re so excited to have Madi running with Team Pencils of Promise and grateful to everyone cheering her on along the way.

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