Feature Article | By Jocklyn Mundy | Photos courtesy of Windermere Legacy Fund
How Windermere’s Beloved Wine & Dine Event Grew Into a Legacy Fund for Generations
The Windermere Legacy Fund: L-F Sean Murphy, Kelley Duell, Bill and Pam Martini, Molly Rose, CT Allen, and Debi Lake
Every century leaves its mark. In Windermere, those marks aren’t just carved in stone monuments but in friendships, in shaded parks, and in projects built by neighbors who care.
That spirit has defined Windermere, and in this Centennial year, it is especially evident. The celebrations of 100 years have reminded residents that each generation has been entrusted with both the beauty and the responsibility to care for it. Every friendship formed, every tree planted, every park bench dedicated, and every community project launched has been part of an unbroken chain of neighborly stewardship. The question now is not only how we honor that past, but how we ensure the legacy endures for the next hundred years.
Lasting Relationships and Legacy
It was out of this heritage and the friendships that tie Windermere together that the idea for the Windermere Wine & Dine event was born. More than a decade ago, a group of friends asked a simple yet powerful question: How could Windermere raise money that would directly benefit the town and its charities, while bringing people closer together in the process?
The answer became Windermere Wine & Dine. What started as a bold vision quickly grew into one of the town’s most loved traditions. Each year, at Town Hall, under the oak canopy, residents gather for an evening of fellowship and philanthropy. Behind the wine glasses and white tents, the purpose was always clear: raising the kind of proceeds that could make a lasting impact.
And it worked. Over the years, Wine & Dine poured its success back into Windermere, supporting town projects, youth programs, and local Central Florida nonprofits. By its 11th year, the event had raised nearly $2 million dollars. The giving became a tradition in itself, inspiring residents to volunteer, participate, and take pride in what their town could accomplish together.
This core group of trusted friends, CT Allen, Sean Murphy, Debi Lake, Pam & Bill Martini, Kelley Duell, and Molly Rose, “The Legacy Team”, all longtime Windermere residents, accomplished something extraordinary. They volunteered thousands of hours, transforming an idea into a signature town institution. Together, they proved that when generosity is the goal, a small group with a big heart can achieve extraordinary things.
Raising a Glass, Passing the Torch
The most respected institutions begin with a bold vision, nurture the idea, and grow it year after year, creating something that endures for generations. That’s exactly what the Legacy Team achieved. What began as a few neighbors with a dream grew into a premier event. But instead of chasing profit, this team measured success in how much they could give away, all while preserving the style, quality, and fun that made Wine & Dine a town favorite.
Prestigious sponsors help make that possible, ranging from acclaimed restaurants and wineries to respected businesses outside the culinary world. Beyond the polish, what stood out most was how deeply the community itself showed up. Wine & Dine became more than a fundraiser; it became a showcase of local excellence, carried forward year after year, strengthening Central Florida nonprofits and uniting the town in pride.
Still, with success came a difficult question: could anyone carry Wine & Dine forward, or would the town face the unthinkable, closing the chapter on an event that had given so much good to so many?
CT Allen and Stephen Lewis
That’s when Town Manager Robert Smith suggested exploring the West Orange Foundation, the philanthropic arm of the West Orange Chamber of Commerce. The timing proved serendipitous. The Chamber was entering a new era under the leadership of Windermere Town Resident Stephen Lewis, who brought fresh vision and a collaborative culture. CT recalls that her early meetings with Lewis gave her confidence. His capability, his respect for the event’s legacy, and his focus on community impact convinced her that the Wine & Dine could continue with the same quality and care.
The agreement that followed ensured continuity. The West Orange Foundation would assume management of Wine & Dine, preserving its identity and traditions. In return, 25 percent of net proceeds would flow back annually to the Windermere Legacy Fund, a permanent foundation dedicated to carrying forward the tradition of giving.
“We built Wine & Dine over more than a decade,” CT says. “It carries a legacy of trust. We wanted to be sure it remained something our town could be proud of.”
For CT, the partnership was both practical and hopeful. With the West Orange Foundation’s infrastructure and resources, Wine & Dine could grow even further, while Windermere residents could be assured the event would always remain tied to their community.
Pam Martini shared: “Bill and I are so proud to see all the hard work of all the Wine and Dine Committee members over the past 11 years culminate in the creation of this ground-breaking Windermere Legacy Fund. WWD has been a labor of love for all of us not only to create the signature event of the year where our community can come together to raise funds for great local charities (and let’s face it, have a great party!) but the Legacy Fund will take it to the next level to actively engage the community in creating new opportunities for giving back. Our hope is to inspire the next generation to pick up where we leave off.”
Donation to Do Good Farms
Donation to Second Harvest Food Bank. We gave them a $50,000 check during COVID to restock and launch their drive-up food delivery initiative.
Donation to Second Harvest Food Bank
We delivered $2000 checks to each food pantry during COVID to restock their food, as many schools were closed and a lot of kids who relied on breakfast and lunch at school were without. We helped establish a pickup from those schools in West Orange for the kids who needed it.
Building the Windermere Legacy Fund
While the Windermere Wine & Dine event found new stewardship through the West Orange Foundation, CT, and the committee had been planning something closer to home. They wanted to ensure that Windermere itself would always benefit from the generosity generated by the event. Anticipating the inevitable, they began setting aside funds for the day when Wine & Dine would transition. By the close of the 2024–25 season, the financial seed that would become the Windermere Legacy Fund (the Fund) was planted.
The structure was intentional. The Legacy Fund is not meant to replace Wine & Dine, but to extend its values, transforming an annual evening of generosity into a year-round commitment to the town and local charities. CT insisted that the Fund’s executive board include the sitting Mayor of Windermere and the Town Manager, not individuals by name, but the offices themselves, so Windermere would always have a voice at the table. Alongside them sit the members of The Legacy Team, serving as the Fund’s inaugural resident leaders. As these founding members eventually rotate off, their seats will be filled exclusively by other residents of the Town of Windermere, ensuring the Fund always remains rooted in the community it was created to serve. At its helm, CT Allen serves as chair, guiding the Fund in its first chapter while preparing to one day pass that role on to another resident leader.
To establish the Legacy Fund on a solid footing, the team turned to trusted partners. Legal counsel was provided by Gray/Robinson, a firm long associated with the town, while financial stewardship was entrusted to David Brinckerhoff with the Brinckerhoff Financial Group of Raymond James, who also manages the Windermere Police Foundation. This continuity provides both credibility and peace of mind.
CT is quick to point out, “Town Manager Robert Smith was instrumental in supporting Wine & Dine from the beginning; he was also very helpful in navigating the legal work with establishing the Windermere Legacy Fund.” From the start, Robert embraced the vision, helping navigate logistics, fostering town partnerships, and ensuring the event had the structure it needed to thrive. His steady leadership became a constant thread, quietly but critically strengthening both the committee’s work and the community.
CT reflects, “Wine & Dine was never just about an event; it was about giving. Over time, the event evolved to the point where we could return more than $200,000 annually, which had a profoundly positive impact on every level: for the town, our committee, and the community. That’s why we kept doing it. The goal was always to keep the giving going.”
A Mission Rooted in Community
At its heart, the Windermere Legacy Fund is about carrying forward the tradition of giving that Wine & Dine established, channeling proceeds back into the community to support charities that strengthen families, educate children, and inspire a culture of service. Though Windermere may appear idyllic, just beyond its borders are countless organizations serving children, seniors, and families in crisis. The Legacy Fund was established to bridge that gap, enabling residents not only to provide financial support but also to engage more deeply through volunteerism and leadership. The vision is for neighbors to invest their time, serve on nonprofit boards, and step into roles that will strengthen the wider community for the next century.
One of the Fund’s defining features is its resident-driven model. It prioritizes neighbors who are personally invested, those serving on boards, guiding programs, or leading nonprofits, ensuring that support flows through people already making a difference. The philosophy is simple: giving is strongest when it flows through personal commitment. By investing in causes where residents are already engaged, the Fund ensures accountability while deepening community ties.
From the outset, the Fund has taken a careful, future-focused approach. Rather than drawing down its principal, it will distribute only from annual earnings, protecting the core investment while allowing steady growth. With this strategy, and with ongoing Wine & Dine proceeds and new contributions, the goal is to build the Fund to $1 million in assets, creating a lasting resource that will serve Windermere for generations to come. It is, in every sense, an investment in the town’s future, ensuring that the generosity of today becomes the legacy of tomorrow.
Educating the Next Generation
The Windermere Legacy Fund is not only about giving; it’s about growing a culture of service. Just as Wine & Dine inspired neighbors to see what was possible when a community worked together, the Fund seeks to make that tangible for new generations.
Future plans include community gatherings where local charities can share their missions and residents can discover meaningful ways to get involved. The vision is simple: families walking through Town Hall, where charities have the opportunity to share their vision, their needs, and their opportunities for service. Children learning alongside their parents that generosity begins at home, and neighbors find causes that align with their passions.
“So many people want to give, but they don’t know where to start,” CT says. “We can make it easier.”
The goal is not just to fund projects, but to foster a habit of volunteerism, ensuring that Windermere’s legacy of giving is passed down.
First Initiative: Giving Back Together
The Windermere Legacy Fund will launch its first initiative this month, in partnership with the Windermere Police Foundation. On October 18th, the Legacy Fund will join Chief David Ogden in supporting the Build-A-Bed project, now in its fifth year.
In honor of Windermere’s Centennial, the goal has been expanded this year to 100 beds for 100 years, more than double the usual effort. More than 200 volunteers will join the effort, turning Town Hall into a workshop alive with hammers, drills, and teamwork. Each bed built will come complete with bedding and be delivered to a child in need in Central Florida.
For the Windermere Legacy Fund, helping Build-A-Bed reach its most ambitious goal yet was the ideal first project to support. This project defines the Legacy Fund’s vision of involving the community in volunteerism.
“To have the support of the town and now the Legacy Fund means everything,” Ogden explains. “This project has always been about helping children sleep safely and with dignity. What makes it powerful is seeing our residents come out: families, young people, retirees, all working side by side. That kind of community support is what makes Windermere so special, and it’s why this project continues to grow year after year.”
The Spirit of Wine & Dine Lives On
The chalice has been passed, and the legacy remains strong. The Windermere Wine & Dine event, now managed by the West Orange Foundation, retains its legacy, deeply rooted in the heart of the Windermere Legacy Fund. The message that a small town can do big things has never been more alive. “We proved it for more than a decade,” CT reflects. “Now, through the Legacy Fund, we’re carrying that same spirit into the future.”
Looking ahead, the Fund will continue to grow, expanding its base, awarding grants, and creating new opportunities for residents to serve. Each February, Wine & Dine will generate fresh proceeds. Each season, new projects will strengthen connections between our community and nonprofits. Future generations will inherit not only a town, but a culture of generosity.
Windermere’s beauty will always be found in its oak canopy, quiet sand streets, and the sparkling waters of the Butler Chain. Yet its true strength lies in its people, neighbors who show up, leaders like CT Allen, Stephen Lewis, Robert Smith, and Chief David Ogden who inspire others, and the teams who roll up their sleeves to serve alongside them.
The Windermere Legacy Fund ensures that this spirit continues. It is both a symbol and safeguard of what makes Windermere unique: a place where beauty and neighborliness are inseparable, and where legacy is built not for one generation, but for all.
Windermere Wine & Dine Tickets
On Sale: Friday, October 25 at 9:00 a.m.
The 2026 Wine And Dine will take place Saturday, January 31st. Residents are encouraged to act quickly; this beloved event always sells out fast. The Legacy Fund and West Orange Foundation want to ensure Windermere families have the first chance to secure their spot at one of the town’s most cherished traditions.
Stephen Lewis, President and CEO of the West Orange Chamber of Commerce:
“The West Orange Foundation, the philanthropic arm of the West Orange Chamber of Commerce, is truly honored and excited to take the reins of this beloved community event. We look forward to building on the vision and legacy that the Wine and Dine has established over the past 11 years, while honoring the traditions that have made this event so cherished. We are deeply appreciative of the Town of Windermere and the continued commitment to supporting and strengthening the community where we all live, work, play, and do business.”
