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Our Story

What Began as Five Questions Became a Way Forward.

The Story Behind Grace Trail

There are seasons in every life when the path forward isn't clear. Grace Trail began during one of those seasons—not as a program or plan, but as one mother's search for a way to keep moving forward.

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What began as a deeply personal practice would eventually become something others recognized in their own lives.

A Practice Takes Shape

What began as five questions slowly became a rhythm Anne returned to each day.

While her son was serving in combat in Afghanistan, Anne found herself searching for a way to move through uncertainty rather than simply endure it.

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She began returning to five simple questions—questions that didn't offer easy answers, but gave her somewhere to place her fear.

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As the questions became part of her daily walks, something shifted: the answers often came while she was moving.

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"Where can people go to walk, reflect, and find their footing during hard seasons of life?"

The Walk Became the Trail

Five questions. Five stones. One walk that was becoming something more.

As Anne continued walking the Plymouth waterfront, the questions became inseparable from the path itself. She began writing each one onto a stone and placing it where it had become meaningful in her own journey.

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Soon, her husband began walking with her. The questions gave them a language for conversations that weren't always easy to begin.​

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Others Began Walking

People began finding themselves in the questions.

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Neighbors, friends, and visitors began stopping to read the handwritten stones, reflect, and return.

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What had begun as Anne's personal practice was becoming something shared.

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The questions weren't telling people what to think. They were creating space for people to discover their own answers.

From Temporary Stones to a Permanent Trail

The community's response transformed a personal practice into a permanent place for reflection.

The Town of Plymouth recognized Grace Trail as a valued community resource and partnered with Anne to establish the first permanent Grace Trail along Plymouth Harbor.

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With the support and craftsmanship of local partners, the handwritten stones evolved into permanent granite markers—preserving the five questions for generations to come.

Our Story Continues

The five questions remain at the heart of Grace Trail. Where they can lead continues to grow.

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What began along the Plymouth waterfront now reaches people in communities, schools, workplaces, healthcare settings, and beyond—through permanent Trails and new ways to bring the practice wherever people are.

Coming Full Circle

The journey that inspired Grace Trail continues to shape where it grows today.

Borckton VA Grace Trail Wellness Installation Fall 2026

Years after first walking into the VA seeking help for her son, Anne returned with something shaped by that very journey.

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Today, the first Grace Trail within the Department of Veterans Affairs is taking root at VA Boston's Brockton campus.

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For Anne, it is more than another Trail. It is a reminder that some of life's most difficult experiences can become the beginning of something that helps others.

Take the Next Step

Walk a Trail, experience the five questions, bring Grace Trail to your community, or discover more of Anne’s work.

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Experience Grace Trail

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Explore guided experiences, workshops, and meaningful ways to engage with the five questions.

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Find a Trail Near You

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Discover Grace Trails in communities across the country and experience the five questions for yourself.

Umass Boston Grace Trail Student Walkers

Bring Grace Trail to Your Community

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Explore what it takes to create a Grace Trail where you live, work, learn, or serve.

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Meet Anne Jolles

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Meet the woman behind Grace Trail and explore her books, speaking, and work.

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