Telling Old Town's Story: FOOT and the Heart of Winchester
Published on September 03, 2025
Walk down Winchester’s historic walking mall and you’ll see more than brick sidewalks and 18th-century architecture. You’ll see the work of neighbors who care deeply about their community. People who believe Old Town can be more than a shopping destination. It can be a shared story.
Friends of Old Town, also known as Winchester Main Street, is the nonprofit at the heart of that story. Born out of a desire to give Winchester’s Main Street program more community voice and creative direction, Friends of Old Town has quickly grown into a local force for good things in our city.
Their mission is to make Old Town not only historically preserved, but vibrantly alive with art on the walls, music in the air, and people in the streets.
In 2023, Friends of Old Town officially took over the Main Street program from city administration and ushered in a new era of grassroots energy and volunteer-led ideas. But they didn’t just take the reins. They got to work reimagining what public space in Old Town could be.
They launched a long-range master planning project with one goal in mind: to listen. What do residents want from Old Town? What makes it feel welcoming, beautiful, and distinctly Winchester?
Through public forums, design sessions, and old-fashioned conversations on the bricks, Friends of Old Town invited the community into the process and started turning feedback into action.
At the same time, they made sure Old Town didn’t just look good on paper. It had to feel good in real life. From organizing the annual events like Kidz Fest and First Fridays, bringing live music and family-friendly vibes to the mall, to the creation of the “History of Us” walking tour, featuring QR-coded stories in business windows, they centered every project around connection.
Winchester’s history runs deep, and Friends of Old Town sees public art as a way to bring that legacy into the present. Rather than separating history and creativity, they use public art to highlight, reinterpret, and celebrate the stories that have shaped this place. Projects like History of Us, our self-guided walking tour, invite people to explore the lives, buildings, and businesses that form the backbone of Old Town, often in ways that surprise and inspire. From murals centered on themes like childhood literacy to pop-up performances and storefront storytelling, they treat Old Town as a living gallery. Every installation is a chance to connect heritage with imagination and to invite the community into the story.
They’ve also created space for dialogue. From community meetings about public art and preservation to open discussions on revitalization, Friends of Old Town has made it clear: change isn’t something that happens to the town. It’s something that happens with it.
In just one year, Friends of Old Town has redefined what it means to steward a Main Street. They’ve done the big things like strategic planning, nonprofit structuring, and event development. And they’ve done the little things too, like chatting with shop owners on a Tuesday afternoon to see how business is going.
They’ve shown that revitalization doesn’t have to come from a grant or a headline. It can come from a neighbor showing up, a volunteer giving their Saturday, or a nonprofit making sure downtown feels like home.
Change in Winchester isn’t something that happens to the town. It’s something that happens with it.
As 2025 unfolds, the story of Old Town continues. And thanks to Friends of Old Town, it’s a story more people are excited to write together.
BY BRADY CLOVEN Executive Director, Friends of Old Town