Run Among the Lakes: Celebrating 25 Years

Photography by Windermere Photography

On the morning of Saturday, October 10, more than a thousand people gathered on Main Street before sunrise and waited for the horn. Some have been doing it for twenty years. Some were doing it for the first time, talked into it by a neighbor, a spouse, or a resolution that finally caught up with them. When the horn sounded, all of them ran out onto the same sand roads that have carried this race since 2002.

The Orlando Health / Town of Windermere Run Among the Lakes turned twenty-five this year, and the town marked the occasion the way Windermere marks most things that matter: together, on its own home ground, with neighbors showing up for one another and cheering at every turn. Twenty-five years in, that spirit has never been in short supply.

Born in a Hard Autumn

The story begins in the fall of 2001, in the weeks after September 11, when the whole country was searching for ways to hold on to one another.

Donna Steele had joined the town's Parks and Recreation Committee, and every committee was being asked to come up with a fundraiser. After the attacks, her idea took on a deeper purpose. "When 9/11 happened, I thought we needed to unite people," she said. "We wanted it to be something fun for the family."

Donna loved art, and she loved sports, and she saw no reason a single morning could not hold both. With a handful of neighbors beside her, she built a race around the town's unpaved roads. The following spring, in 2002, the first Windermere Run Among the Lakes set out beneath the oaks.

One custom from those first years has never changed. When the bibs are handed out, number one belongs to Donna Steele. It always has.

Art You Can Wear

Because the race grew from a love of both art and sport, it carried art from the start. Each year, local artists contributed original pieces that reflected nature, community, and the landmarks residents knew by heart, and that artwork often became the face of the race shirt.

The early years favored traditional work. Today the artwork is just as likely to be photography or a digitally enhanced image. The subjects, though, have stayed faithful to what matters most to the town.

This year's image carries a deeper meaning. It features Old Glory, the red, white and blue horse that has long been one of Windermere's most beloved landmarks, and it now honors hometown hero U.S. Army First Lieutenant Evan Fitzgibbon. Evan grew up in Windermere, and his family's home sat just behind that horse on Oakdale Street. For years, his mother gave visitors directions by telling them to look for the red, white and blue horse. Evan graduated from West Point and was training at Army Ranger School in Georgia when he lost his life in August 2022, at just 23 years old. His favorite verse, Proverbs 21:31, speaks of a horse made ready for the day of battle and a victory that belongs to the Lord. In January 2025, Old Glory returned to the town square as a permanent memorial in his name. This October, more than a thousand runners carried his memory along the sand roads he knew as a boy.

A Race That Grew Up Here

For more than a decade, the run kept its springtime rhythm, a 5K on hard-packed sand and clay that drew families, neighbors, and a growing number of visitors who had heard about the course.

In 2017, after residents asked for more distance, organizers added a 10K. The race later moved from spring to fall, gained Orlando Health as its title sponsor, and settled into the second Saturday of October, between the first cool mornings and the holidays.

Growth came steadily rather than suddenly. The 2021 twentieth anniversary drew 900 registrations. By 2023, the race sold out at 1,200. Last year it doubled as part of the town's centennial celebration. This year, it sold out again.

The field has grown more varied as well as larger. "We've had 7-year-olds and 87-year-olds running," Sue Ann Reichard has said. The 5K tends to draw recreational runners and walkers, while the 10K attracts the more competitive crowd. There is room for all of them.

Twenty-five years is long enough for a race to become a habit. Long enough for a child who ran the Kids Run to come back for the 10K. Long enough that families plan their Octobers around it.

The Course Has Always Been the Point

There is no shortage of road races in Central Florida. There is exactly one that runs on hard-packed sand and clay beneath century-old oaks, with Lake Butler, Lake Down, and Lake Bessie appearing between the trees around nearly every bend. The 10K adds a stretch along Lake Butler Boulevard. The 5K keeps to the heart of town.

Runners often remark on how beautiful the course is, especially at sunrise, when the light filters through the oaks and catches the water.

This year’s race came with a test of its own. The heavy rains from Hurricane Isaias soaked the course in the days leading up to race morning, and the 10K had to be cancelled. Then, on race day, the clouds parted. The 5K and every other event went on as scheduled under dry skies. All registered participants received a custom event T-shirt and a commemorative finisher medal designed for the anniversary, sponsored by Simon Simaan Group Real Estate.

The Hands Behind It

Nothing about this race is produced by an outside company. It is built, year after year, by the Town of Windermere Parks and Recreation Committee, a group of residents who give their time without pay and with very little fanfare.

Their work reaches far beyond one Saturday in October. The committee helps look after the parks, beaches, and trails that give Windermere much of its character, and it works to keep those spaces welcoming for everyone who uses them. Its members put on the Halloween Costume Parade and Hayride, along with other gatherings that fill the town calendar. When a playground needs new equipment or a park needs shade, this group often finds a way to make it happen.

Leadership has passed through careful hands. Donna Steele founded the race and chaired the committee. Nora Brophy led it in more recent years. Today Dena O'Malley and Sue Ann Reichard serve as co-chairs, carrying the founder's vision forward. Dena has been part of this race for years, first as a volunteer coordinator at a folding table with her own kids helping out. That progression says a great deal about how the event runs. The people who build it are the same people whose families will use the parks it improves.

Alongside the co-chairs, the committee includes Maggie Dimino, Kelley Duell, Jill Ata, Tracy McLaughlin, Jen Kirby, and Jeanne Marie Olache. Some of them run it, too. In 2024, Kelley Duell finished first in her age division.

"Every single dollar raised goes back into our parks. It's truly a labor of love for our volunteers," Dena has said.

On race morning, that labor becomes visible. Volunteers arrive before daylight to direct parking, fill cups, cheer at the turns, and hang medals around the necks of people they have never met.

Every hour of it is donated. The work these eight women did in the months before October is the difference between a nice morning and a race that sends real money back into Windermere's parks. The town is fortunate to have them.

Where the Money Goes

The reason the race exists has never changed. Its proceeds support the Town of Windermere Parks and Recreation Department, and the results are visible to anyone who spends an afternoon in a Windermere park.

In one recent year alone, the run returned close to $20,000 to the department. That money funded volleyball courts and a dock for swimming and fishing at the Windermere Recreation Center. Other years have paid for playground renovations, shade structures, field maintenance, and the steady work of keeping the town's parks in the condition residents expect.

A shaded playground. A dock where a child catches a first fish. A bench with a family's name on it. Those are the results that outlast any finish time.

"The Run Among the Lakes is a Windermere tradition where the benefit comes right back to our community. Proceeds help our Parks & Recreation Committee and Public Works team improve the parks, playgrounds, docks, and courts our families use every day. We have a great morning together, and the good it does lasts long after the last runner crosses the finish line."

Mayor Andy Williams

The Names on the Banner

A race of this size runs on its sponsors, and this year's roster reads like a walk down Main Street and out into the wider community.

Magnifica returned as the 25th Anniversary Community Impact Sponsor, an investment aimed not just at race day but at year-round community programming. Chick-fil-A sponsored the Kids Run. Simon Simaan Group Real Estate sponsored the anniversary medals. Windermere Brewing took on the After Race Cheers, the newly renamed post-race celebration.

Hydration stations were covered by Lakeside Realty on the 5K course and West Orange Roofing on the 10K.

Rivian Row

New this year was an exclusive automotive sponsorship, and Rivian took it.

Rivian Row occupied a dedicated display area directly south of Town Hall, where attendees could walk through several vehicles, step inside, look at cargo space, and talk with product specialists about charging, ownership, and available models. Rivian representatives were on hand throughout race day, and a smaller Rivian Row greeted runners at packet pickup as well.

A brand built around exploration, meeting a canopy road at seven in the morning, is a reasonable definition of a good match.

Miles, Mimosas & Mingling

The anniversary brought something the race has never had before.

Immediately after the run, Solvino hosted a ticketed brunch in the Solvino Courtyard, directly across Main Street from the finish line. Billed as a 25th anniversary block party, Miles, Mimosas & Mingling was an intimate gathering for guests ages 21 and older.

Tickets were $50 per person and included mimosas, juice, and contributions from Jeff's Bagels, Fresco's, Pistil, Penelope's, and Victoria Jewelers. Each ticket also included reserved parking behind the Plaza, which may have been worth the price alone on race morning.

You didn’t have to run to attend, and 100% of the proceeds went directly to Parks and Recreation.

The Smallest Runners

The Kids Run remains free for children ages seven and under, with no registration required. The youngest finishers cross the line to a round of applause just like their older counterparts.

For many Windermere families, this is where the tradition begins.

How to Be Part of It

If you came out to cheer on the participants, you were in good company. Bring a lawn chair, find a spot along the course, and join the neighbors who line the route with homemade signs and encouragement for each runner who passes. Some of the best seats in town are at the end of a driveway on race morning, and the spectators often have as much fun as the runners.

Still Among the Lakes

Windermere has changed a great deal since the fall of 2001. The town has grown, the race has found its October home, and a field that once fit easily along a few sand roads now fills Main Street before first light. Yet the roads are still unpaved. The oaks are twenty-five years older. The lakes look the same at daybreak as they did the morning the first runners passed them.

This was never meant to be only a race. It was intended to bring neighbors and the extended community together. In the years since, a small circle of volunteers has carried that idea forward, and each October it has left something good behind.

Keep an eye out for bib number one. As always, it belongs to Donna Steele, and if you spot it, take a moment to thank her. Watch, too, for the red shirts bearing the race logo. Each one is worn by a Parks and Recreation volunteer who gave their time so the rest of us could enjoy the morning. They never ask for thanks, which is exactly why they deserve it.

It began as a way to bring a town together. Twenty-five years later, it still does exactly that.

25th Anniversary Run Among the Lakes Sponsors

Title Sponsor: Orlando Health

Signature Sponsors: Windermere Brewing, Magnifica, Chick-fil-A, Simon Simaan Group Real Estate, Solvino's

Premier Sponsors: Windermere Preparatory School, Rivian

Hydration Station Sponsors: Lakeside Realty Windermere, West Orange Roofing

Associate Sponsors: Neighbors of Windermere / Butler Chain Living, The Real Estate Collection, Victoria Jewelers, Sorenson Construction, Kalos Services, Law Office of Pamela Martini, Healthy West Orange, Family Church, West Orange Chamber of Commerce, DASH Sports, Family Life Counseling Center, Penelope's Coffee & Baked Goods

Patron Sponsors: Orange County Library System, Lindora Windermere-Metabolic Health + Wellness, Performance Driven Therapy & Chiropractic, Toole's Ace Hardware, Fresco Pizzeria, Jeff's Bagel Run, Tolan Insurance Group, Pistil, Woofies, Wonderly Lights and Hotwire Communication