Cover Article | By Jocklyn Mundy | Photos courtesy of Valentin Mellstrom
On the cover: Centennial Committee (R-L) Gregg Anderson, Tonya Elliot Moore, Molly Rose, Chris Sapp, Kim Hawkins-Head, Deputy Chief Jayson Bonk, CT Allen, Bill Martini, Andy Williams. Not Pictured (Dorothy Burkhalter and Debi Lake)
Windermere’s Centennial Celebration continues to unfold as a year-long tribute to the town’s rich history, cherished traditions, and vibrant community spirit. Through a thoughtfully planned series of events—ranging from historical storytelling and exhibits to community projects and themed gatherings—the celebration invites residents to engage with Windermere’s legacy in meaningful ways. Spearheaded by a dedicated Centennial Committee, the effort aims to preserve the character and values that have defined Windermere for the past 100 years while inspiring a renewed sense of connection and pride for future generations. Each moment, memory, and milestone shared throughout the year is a reminder of what makes this small town truly special.
As Windermere’s historic Centennial year approached, it was clear who should help lead the celebration—longtime resident and community powerhouse CT Allen. Known and loved for her tireless dedication, CT has a long history of bringing people together for a greater purpose. Over a decade ago, she founded the Windermere Wine & Dine, now one of the town’s most anticipated and beloved annual events, created to support local causes and celebrate community spirit. Her natural leadership, contagious energy, and deep-rooted commitment made her the perfect fit to help guide this once-in-a-century moment.
“What motivated me to join the Centennial Committee?” she said with a grin. “To be part of something special that only comes along… well… every 100 years.”
CT is quick to downplay any title, suggesting she’s “in charge.” As she often says, “Each member shares the vision and responsibility equally.”
From the steering committee's first meeting in May last year, this has been a labor of love for everyone involved. CT explains, “We wanted a diverse group of individuals that would give voice to their respective areas. You will see the Police Department, Public Works, Town Admin, Councilman, and Residents involved. Some were asked to join for their specific skills, such as Molly Rose, an excellent project manager and finance person who keeps the budget and the dollars straight. Kim Hawkins-Head is a fantastic graphic artist who has helped create the Centennial's look and brand. Dorothy Burkhalter’s knowledge of the town's history was invaluable. Everyone on the committee has a passion for the town, which led to this group being very cohesive and genuinely working as a team with no egos involved. They are all doers. None of us have titles; we have responsibilities, and each takes ownership of specific projects or elements of projects. We lean into each other’s strengths and experience.”
The Centennial Committee’s resident members include current Town Council Member Andy Williams, former Council Member Bill Martini, Windermere Rotary Club President Gregg Anderson, local business owner Chris Sapp, former Council Member Molly Rose, Debi Lake, and Kim Hawkins-Head. They are joined by key members of the town staff: Town Clerk Dorothy Burkhalter, Director of Public Works Tonya Elliott Moore, and Deputy Chief Jayson Bonk. The all-volunteer committee began meeting monthly in early 2024, eventually shifting to weekly as the Centennial approached.
The first sign of Windermere’s Centennial year arrived quietly but meaningfully as the town welcomed 2025 with newly unveiled Centennial branding and signage. Festive banners featuring the Centennial logo were hung along light poles, and refreshed entry signs offered a proud tribute to Windermere’s 100-year legacy. These visual touches transformed everyday spaces into lasting reminders of the town’s rich history.
The official kick-off to the Centennial year was the January Torch-Lighting Ceremony at Town Hall. Local and state officials gathered to witness the symbolic lighting of the Centennial Flames, which will remain lit throughout 2025. Mayor Jim O’Brien hosted the event, joined by State Representative Leonard Spencer, who presented a proclamation from the Florida House. And Orange County Mayor Jerry Demings officially declared January 24 as Town of Windermere Day in Orange County. Town Manager Robert Smith and Commissioner Nicole Wilson also shared at the historic event.
Adding a meaningful touch to the ceremony, John Palmer Luff Jr., great-grandson of town founder John Calvin Palmer, joined Mayor O’Brien in lighting the commemorative flames—bridging Windermere’s storied past with its promising future.
Just days earlier, the Windermere Tree Board hosted a Centennial Tree Giveaway for residents, distributing native species like Longleaf Pine, Live Oak, and Bald Cypress. Each tree featured a commemorative plaque and contributed to the creation of a “Legacy Tree Walk”—a living, growing tribute to Windermere.
In February, the 11th Annual Windermere Wine & Dine took on added significance as the first major community celebration of the Centennial. Under the town's oak canopy and twinkling lights, over 1,200 attendees enjoyed fine wines and cuisine from Central Florida’s premier chefs. The event has become a cherished tradition, known for its vibrant ambiance and its ability to bring neighbors together under the stars.
The Wine & Dine represents more than just an evening of enjoyment—it embodies a platform for lasting community impact. CT Allen first envisioned the event as a way to raise money to supply much-needed technology to Windermere Elementary and other local schools. Friends fondly recall when she first said, “I have an idea.” More than a decade later, her inspiration has become a legacy of civic pride and a shining example of what happens when a community comes together. The event has since grown into a powerful fundraising force benefiting a range of town committees and Central Florida charities. As always, CT’s signature blend of heart and drive made an impact. With a fundraising goal of $2 million, this year’s Wine & Dine continued to highlight the strength of a community united for the common good.
Following the Wine & Dine, the Centennial Country Fair reunited the community—this time for the whole family. The sold-out event was designed to evoke the spirit of a bygone era, transporting attendees to a simpler time. “We wanted something that reflected the town's soul—family, fun, and a little nostalgia,” said CT “A good old-fashioned country fair just felt right.”
The Pines buzzed with activities for all ages, including a 100-foot slide, inflatable play zones, a flying swing ride, a giant Ferris wheel, and nostalgic carnival games with classic prizes. Though the spring sun made its presence known, the towering pine trees that gave the venue its name provided welcome shade. Families gathered beneath the pine canopy to cool off, chat, and enjoy the company of neighbors with a cold drink and favorite food truck eats.
An undeniable crowd-pleaser was the dunk tank—a throwback favorite made even more entertaining by the nonstop commentary of Bill Martini, affectionately dubbed the “Dunk Tank Barker.” Stationed beside the splash zone from open to close, Martini called balls and strikes with the flair of a seasoned carnival ringmaster, egging on every would-be pitcher with playful taunts and well-timed jokes. “I’ve seen better arms on a T-Rex!” he’d shout, grinning behind his sunglasses. “Are you sure you're not left-handed?”
Windermere Elementary School Principal Janet Bittick volunteered in the tank where students lined up, excited about the chance to soak their principal. Even with Bill’s good-humored warnings— “Just remember, she can give you detention!” “I hope you like extra homework!!!”—the softballs flew.
Also getting dunked for a good cause were Windermere’s Mayor Jim O’Brien, Police Chief David Ogden, Town Councilman Tom Stroup, and Town Manager Robert Smith, who took turns on the plank, raising funds for the Windermere Police Department Foundation with every satisfying splash. It was community spirit at its best—good people, good laughs, and good causes all soaking up the moment (and a lot of water).
The main stage entertainment brought steady energy and excitement throughout the day. The Windermere Elementary Chorus opened the fair with a charming performance, setting the tone for a full lineup of live music. John Ashley & The Swamp Bandits, Handpicked, and The Down Brothers kept the crowd engaged with lively sets, all building toward the headlining act—Sawyer Brown. Led by part-time Windermere resident Mark Miller, the band delivered a dynamic show that transformed The Pines into a full-blown concert experience, with hundreds of fans singing along to every word.
Founded in 1981 in Apopka, Florida, Sawyer Brown gained national fame by winning the grand prize on the inaugural season of Star Search. They carved out a niche in country music with a sound that blends Nashville polish with working-class grit. Over the past four decades, they’ve released 18 studio albums, produced numerous chart-topping hits, and performed thousands of shows across the country. However, this performance was special for frontman Mark Miller because it was personal.
Miller first discovered Windermere’s small-town charm while working for Disney years ago. One drive through town was all it took. Like many residents, he was drawn to the area’s natural beauty and laid-back vibe—but the water sealed the deal. A fan of wakeboarding, wake surfing, and waterskiing, he says living on the Butler Chain of Lakes is a dream come true.
The band’s setlist was a greatest-hits parade— “Some Girls Do,” “The Walk,” “Step That Step.” The energy was electric, and it was clear this was more than just another gig. For Miller and for fans who’d grown up with their music, it was a celebration not just of the town’s 100 years, but of decades of shared memories set to a familiar beat.
As part of its Centennial celebration, the Town of Windermere extended a special invitation to 44 children and staff from Edgewood Children’s Ranch, giving them an afternoon they won’t soon forget. Many children at the Ranch have experienced difficult personal journeys, and the opportunity to enjoy a carefree day at the fair was a gift of joy and escape. The town provided entrance tickets, game coupons, and cowboy hats to help them blend right in with the fair’s festive atmosphere. From the thrill of carnival rides to the simple delight of winning a prize, every child could experience the event's magic. To complete the day, the town also covered dinner for the entire group—a gesture that didn’t go unnoticed.
Bruce Jordan, Executive Director of Edgewood Children’s Ranch, shared his deep appreciation. “This is more than just a fun day for these kids,” he said. “It’s a chance to feel joy and belonging and to be reminded that they matter. We are truly thankful to the Town of Windermere for making this possible. The support means the world to us—and the children.”
Jordan noted that experiences like these leave lasting impressions and help build confidence and a sense of connection to the community—something the Ranch works to instill every day. The town’s sponsorship reflected more than generosity—it was a meaningful reminder that Windermere’s Centennial was about more than looking back. It was about reaching outward, including everyone in the celebration, and sharing the heart of what makes Windermere a truly special place.
As the Centennial year continues, regular town events will be rebranded and enhanced to celebrate. The Town Administration Building’s Centennial Lobby features special exhibits. A highlight is a collection of four commissioned oil paintings generously loaned by longtime resident John Nabers. The artwork depicts significant historical buildings integral to Windermere's heritage, offering residents and visitors a visual journey through the town's architectural evolution.
Complementing the paintings is a looping slideshow with over 300 historical photographs accompanied by oral histories recorded by residents. This multimedia display, created by Chris Sapp, captures the stories and events that have shaped Windermere, providing an immersive experience that connects the community with its past. A selection of apparel and memorabilia is also available for purchase, giving residents a meaningful way to take home a keepsake from the year-long celebration.
From the first flicker of the Centennial Flames to the final notes of “Some Girls Do” at the Fair, the town's past and present residents are part of something lasting—etched not just in the history books, but in hearts.
Thoughts From The Centennial Committee
Asked what the most rewarding part of the Centennial planning has been, CT Allen replied without hesitation: “The ones who raised their hands and volunteered love this town and all the folks who make it so special. With that being the group's foundation, working together became a joy. I knew some well beforehand, and some not so well… working closely with all of them every week since last May, I don’t consider us a committee anymore. We are all friends.”
For Tonya Elliot Moore, one of the Centennial Committee’s key staff members, Windermere’s ability to honor its past while embracing the future stands out the most. “I love how the Town has preserved its roots while adapting over time,” she reflects. “The fact that Town Hall—built in the early 20th century—is still the heart of civic activity today speaks volumes. That continuity really connects generations.”
Resident Kim Head joined the Centennial Committee to give back to the community she loves. From torch-lighting ceremonies to pancake breakfasts, she celebrates the ‘old-Floridian vibe’ that sets Windermere apart. Designing the Centennial calendar taught her more about town history than she ever expected—and deepened her connection to the place she proudly calls home.
