Feature | By Jocklyn Mundy | Photos by 3 J Photography
For as long as most can remember, the pathway from downtown Windermere to Windermere Elementary came down to one narrow crossing over the canal between Lake Down and Wauseon Bay. A steep concrete ramp. A walkway hemmed in by warped chain-link. It was wide enough for two people standing shoulder to shoulder and not much more.
After years of grant applications and budget votes, of drawings revised and revised again, of a certification the town had to earn before it could run the project at all, Windermere has something beautiful. Town staff, mayors and council members worked together across multiple administrations to see it through.
The old bridge is gone. In its place, set into the exact spot where a train trestle once carried the railroad over the water, stands a wide steel bowstring bridge that two golf carts can pass on at once. It opened the first week of August, just days before the first day of school. For all the years it took to get here, that was the deadline that mattered most.
Neighbor in the Hard Hat
On site this summer, John Fitzgibbon was easy to spot, white hard hat with the Windermere town crest on the front, doing what he loves for a town he loves more.
He serves the Town of Windermere as its Town Consultant Engineer. If something in Windermere is being built, rebuilt, or kept from falling down, there is a good chance John has walked it and measured it.
"I love what I do, and this is just logistics," he says.
He is a gifted engineer who spends few of his words talking about engineering. Ask him about the Ward Trail, and he talks about Windermere's incredibly talented staff and how blessed the town is to have them.
Underneath It All
A position with Universal Creative brought John and Cindy to the area. They initially settled a few minutes from Windermere. John recalls that he and Cindy would drive through the Town of Windermere and say, "One day we will move here." That day came in 2000.
Eventually John went out on his own, building a career that extended well beyond traditional engineering. He expanded to Games and online simulations. To John, engineering has never sat in one lane.
Over the years, he has put much of what he knows to work right here in Windermere. Most of that work is far less visible than a bridge.
Stormwater plans. Roadways. Drainage. Drawings carried to council, revised and carried back again. Solutions that have to move water while protecting the sand roads. Nobody stops on the sidewalk to admire a culvert.
But a town depends on what runs underneath it. The water has to go somewhere. The roads have to hold. It takes a team to care about that. The meetings happen on ordinary Tuesday evenings, with a Zoom link open and residents listening as John explains a design, a problem, and a way through it.
Windermere has long understood stewardship. People come here, fall in love with the town and accept a responsibility to leave it better than they found it without losing what made it worth protecting in the first place.
John and Cindy Fitzgibbon have made that responsibility part of their life here.
Where the Trestle Stood
The town considered many bridge styles before the council made its selection.
They chose a bowstring, a form dating to the nineteenth century. Its steel arch rises above the deck much like railroad bridges once did, and against the canal and the oaks, it feels less like something imposed on the landscape than something returned to it.
Long before this was a school route, it was a rail line, and the trestle that crossed this water carried the trains that helped build the community growing around it. The new bridge sits in that same location.
If you look below the bridge at the water's edge, the past is still sitting there. Old railroad-tie abutments, weathered and unglamorous.
"We've intentionally left the old train trestle abutments underneath it," John says, "just as a general reminder of the history."
The trees got the same intention. Before the first machine touched the corridor, the town's Tree Board walked the alignment on foot, marking the trees that would remain and those that could not. In a town that measures itself in canopy, that walk mattered as much as any set of plans.
Ten Weeks
Everything about the Ward Trail moved slowly until the moment it could not.
The planning took years. Crews broke ground in February. And then the whole of it narrowed down to a single window that nobody on the project got to choose.
The crossing could only be removed while school was out.
Children use that route to reach Windermere Elementary. There was only one time frame. It had to come down after the last bell of the school year and had to be ready to carry children before the first bell of the next.
Roughly ten weeks. Every organization involved had to hit the same window at the same time, and none of them could go first.
The engineering came first. The abutments that would receive the new span had to be pre-formed and then integrated on site, and they had to be perfect.
"Everything had to be within micro inches," John says, "so that when the bridge came in, we were able to set it right in place."
Getting the bridge to Windermere was another challenge. The enormous bowstring arrived through town as an oversized load.
The old crossing had to come out on the same day the new one went in. The crane had to be sized precisely and brought into a tight, awkward site, with the canal below and no margin for error.
"As soon as we took the old pedestrian bridge, that's when we've been having a go, go, go," John says. And they went.
Crews pushed the trail toward the school, poured sidewalk, opened the golf cart and pedestrian access over the canal, and worked toward an August target that never moved. On the last Friday in July, with concrete trucks lined up on the site and the landscaping still to go in, John called it an “all-out blitz.” The trail and the bridge opened on August 6. Windermere Elementary started its year on August 11.
After all those years of planning, approvals, funding, and construction, the margin came down to five days.
Maryann, Tony, and Benny Davit enjoying the Ward Trail
The Work No One Sees
When John talks about how the project happened, two names come first. "Without Robert and Tonya, we would have never been able to do it," he says.
Robert Smith, Windermere Town Manager, spent years securing the appropriations that funded the project through the Safe Routes to School program. Tonya Elliott-Moore, Assistant Town Manager and Public Works Director, carried the administrative weight of it, which in a project like this one is no small thing.
The Ward Trail is a Florida Department of Transportation LAP project, which stands for Local Agency Program, and it is not a certification a small town picks up casually. The town itself has to qualify, and to get there, town staff had to complete an extensive slate of FDOT trainings and hold those credentials through the life of the project.
"People don't understand the depth and amount of work that goes into a project behind the scenes," Tonya says. "You can see a project coming to life when it's under construction, but you have no idea the intensity that it took just to get us to the point where that shovel was able to turn."
John worked those same years, and he does not describe any of it as a burden.
"It's been a team, between our engineers and the contractor and our engineering inspection firm, and FDOT coordinating with us," he says. "So it's been a lot, but it's been beautiful."
John cannot say enough about the town staff, about the professionalism and care each of them brings to the job. Past and present council members. The Windermere Police Department. Travis Mathias and his crew in Public Works. Kimley-Horn, the town's engineers, who answered every question as fast as the town could ask it. The contractors, who pressed through the summer. Former Mayor Jim O'Brien, who was instrumental in bringing the project.
Current mayor Andy Williams was on the town council while the project was in planning. He walked this very route to Windermere Elementary himself as a boy over the same narrow crossing his own town has now replaced.
Heart of Windermere
For John, public service in Windermere has never been separate from family. To him, Cindy and Sophia, the Town of Windermere is more than home. It is a family that embraced them all, and one that keeps Evan close.
Evan grew up on these streets. Faithful. Steady. A young man a whole town looks up to. A West Point graduate and a qualified Army Ranger, 1st Lt. Evan Patrick Fitzgibbon was twenty-three when he died in a training exercise in the Georgia mountains on August 9, 2022. Windermere speaks his name with admiration and gratitude. He is our Warrior Poet.
1st Lt. Evan Patrick Fitzgibbon
In January 2025, the Dizney family restored and donated Old Glory, the patriotic horse statue, and the town dedicated it in the square as a permanent memorial to Evan.
The Fitzgibbon name will always stand for the heart of this town, and for the sacrifice this country is built on.
The family gives back to the town that holds them. John is one of the board members of Boots & Salutes, a Windermere effort supporting military veterans, first responders and their families, and he and Cindy serve on its committee. The organization raises money to send families to Healing Warriors Week at Wind River Ranch in Colorado.
The inaugural event this past Valentine's night filled The Pines at Windermere with nearly 200 neighbors. John was the auctioneer, keeping the bidding lively and the laughter steady. Visit bootsandsalutes.org for additional information.
Connecting Our Town
In the end, this crossing was never really about steel, grant cycles or micro-inch tolerances, though it took all three to build it. It was about a safe bridge connecting our town.
It is also a Saturday morning walk, a golf cart at dusk, a stroller and a dog and somebody's teenager on a bike. A trail is one of the few things a town can build that puts its neighbors outside together.
Crews will continue working through the fall on the remaining stretches of trail and landscaping. As the corridor fills in, it will look unmistakably like Windermere: longleaf pine, firebush, saw palmetto, and sabal palm. Florida things, in a town that has always known the difference.
There are many people responsible for getting this bridge built, and John Fitzgibbon would be the first to insist their names belong before his.
But there is something fitting about the neighbor in the white hard hat standing beside a bridge built to carry children safely through the town his family chose more than 25 years ago.
He put years into something most of us will cross without ever thinking about what it took to put it there. Perhaps that is the measure of good infrastructure, and good stewardship.
You notice the town.
You notice the water and the oaks. You wave to the neighbor coming the other way. You watch your children cross safely.
And you never have to think about the bridge at all, and that was always the whole point.
