
About Anne
The Heart Behind Grace Trail
®
A NOTE FROM ANNE
You may be on this page because you’re curious about me — or because something in the idea of Grace Trail resonated with you. Before sharing any titles or milestones, I want you to know this first: this work didn’t begin as a concept or a framework. It began as my life.
During one of the most challenging seasons I’ve ever known, a single word came to me. It happened quietly, in my kitchen, at a time when I felt knocked over and unsure how to take my next step or move forward. Within that word, I began to see a set of questions — simple, familiar, and deeply human. They didn’t feel new. They felt remembered.
Walking became part of that journey. Being in motion — especially outdoors, in nature — helped me disconnect from the noise and reconnect with myself. Movement gave me a way to listen, to be human, and to witness what was actually happening rather than be consumed by it.
Over time, those questions became companions, offering a simple rhythm for moving through life with curiosity, connection, and compassion.
I was simply trying to find my footing. But as I began sharing this way of walking and reflecting — inviting others to pause, to walk, and to ask their own questions — I realized how many people were trying to do the same. In the midst of constant noise, pressure, and expectation, people were longing for a way to reconnect with nature, with themselves, and with one another.
People recognized themselves in the questions. They felt accessible. Grounded. Human.
​
What I came to understand is that people don’t need to be fixed. They need space. And that sometimes, a small set of honest questions is enough to help you stay oriented — to remember what matters and take the next step forward.
Grace Trail grew from that understanding. It took root as a shared, reflective journey — shaped by the people, places, and communities it touches. Whether on a physical trail, in a group, or through personal reflection, Grace Trail offers a way to move through life with greater clarity, connection, and hope — one step at a time.
However you found your way here, I’m glad you did. I hope to see you on the Trail.
With gratitude,


"You don't have to have the answers to understand Grace.
You can be the answer by living your life with curiosity, compassion, and courage."
- Anne Jolles
ANNE'S WORK IN THE WORLD
For more than 25 years, Anne Barry Jolles has worked at the intersection of reflection, leadership, and human resilience.
Her work spans community spaces, national conferences, education, healthcare, and public life — always rooted in presence, listening, and lived experience.
OVER THE YEARS




What began as one-on-one coaching evolved into a movement. Today, Grace Trail brings the same spirit of reflection, perspective, and possibility to thousands of people through trails, communities, schools, campuses, and spaces across the country.
​
​
​
​
​
​
​
​
​
​
2000
2001
2001
2012
2013
2012
2015
2016
2015
2017
2020
2024
2020-2022
2024
2023
2025
2026
2025
2025
Grace Trail is Born
The Grace Trail questions emerge during a personal season of uncertainty, offering a grounded way to pause, reflect, and move forward with intention.
Certified Professional Coach
Anne becomes a Certified Coach through the International Coach Federation and completes training with Coaches Training Institute.

Private Coaching Practice Begins
Anne enters private practice and has since coached more than 2,000 clients.
Massachusetts Conference for Women
Originated “Coaches Corner,” delivering complimentary professional coaching to thousands of women nationwide.
The First Stones Are Placed
Anne places hand-written reflection stones along a walking path in Plymouth, Massachusetts—the future home of the Plymouth Seaside Grace Trail.
International Coach Federation of New England
​Life Coach of the Year · Director Award for Distinguished Service
National Book Publication & Recognition
Publishes "Grace Trail: Find Your Footing and Move Toward the Life You Were Meant to Live".
Massachusetts Conference for Women
Led an interactive Grace Trail experience with six stations and 45 volunteers.
FIGMENT Festival, Boston
Grace Trail installation on the Rose Kennedy Greenway.
International Book Awards — Amsterdam & New York.
Wicked Local ARTY Award · TEDx Wilmington
Recipient of the ARTY Award. Delivered TEDx talk “Cracking the Grace Code.”
Boston University Sargent College
Named Alumnae of the Year.



The First Licensed Custom Trail Installations
During the COVID-19 pandemic, communities sought new ways to foster connection and well-being. The first licensed Grace Trail installations take root across the country, including UMass Boston (MA), Beth Israel Deaconess Hospital–Plymouth (MA), East Lyme (CT), West Woods School (CT), Alpine Shores (WI), Navarino Nature Center (WI)
The First Grace Trail on Private Property
Green Trees Farm (TX) becomes the first private Grace Trail installation and the first location to feature three unique licensed Grace Trails on a single property.
Massachusetts Conference for Women
Created a 50-foot Grace Trail experience engaging over 13,000 attendees.
The Birthplace Becomes Permanent
The Plymouth Seaside Grace Trail is officially licensed, and the original hand-painted stones are replaced with engraved 3,000-pound granite boulders featuring the Grace Trail questions.
A Network of Trailblazers
Licensees begin gathering through community calls and shared initiatives, gaining access to ideas, resources, encouragement, and connections with others bringing Grace Trail to life in their own communities.
National Grace Trail Month Is Established
National Grace Trail Month is created, aligning with Mental Health Awareness Month and activating communities across the country through walks, events, conversations, and opportunities for reflection.
The First Vermont Grace Trail
The Hard'ack Grace Trail is licensed and installed in St. Albans, becoming Vermont's first Grace Trail and the northernmost installation.
National Grace Trail Month Continues to Grow
In its second year, National Grace Trail Month expands with guided walks, community events, media features, and trail activations across the country in support of Mental Health Awareness Month.
2012
A Son's Deployment to Afghanistan
During her son's deployment, Anne found comfort in walking and reflection. The experience later influenced the creation of the first Grace Trail path.











2026
Grace Trail Is Coming to the VA
Installation is scheduled for the Michael M. Lawson Grace Trail at the VA Boston Healthcare System, U.S. Department of Veterans Affairs – Brockton Campus, creating the first memorial Grace Trail and honoring a legacy of service, sacrifice, and remembrance.







