Windermere Wine & Dine to establish Legacy Fund

The Wine & Dine committee hopes to use about $400,000 of the 2024-25 event’s proceeds to establish a Legacy Fund to create a lasting footprint for the town’s future generations.


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The Windermere Town Council at its Oct. 22 meeting discussed the upcoming Centennial Celebration in which the town will commemorate 100 years.

Longtime Windermere resident and Centennial Celebration chair CT Allen gave an update on the celebration plans for 2025.

She said the Centennial Celebration steering committee has challenged the town’s clubs, organizations, committees, businesses and other stakeholders to rebrand next year’s events, or to create new ones, to highlight the centennial milestone. 

“What we want to create for a year with these events is fun for all of the residents, but we also want to inspire the concept that residents will be leaving a footprint for future generations to come,” she said. “Everybody really came to the plate. There’s some really awesome and fun projects out there.”

For example, the town’s Tree Board will give away 100 legacy trees with commemorative plaques to create a centennial tree walk, and the town’s Parks and Recreation Department will create 12 designated centennial benches. In addition, Parks and Rec also will be redesigning the walkway at Central Park with an emblazed centennial logo, and the flags and welcome signs in town will be changed out for the year reflecting the centennial mark. 

A large Centennial Celebration event is planned to take place April 5, 2025, fashioned with an old country fair theme at The Pines, which will include a ferris wheel, dunk tank, carnival games, contests, food and drink, and live music throughout the day. 

With the centennial branding the steering committee is doing, Allen said Wine & Dine also wanted to do its part to celebrate the town’s legacy. 

Going into its 11th year, the event has raised about $2 million since its initial creation.

The Wine & Dine committee hopes to use about $400,000 of the 2024-25 event’s proceeds to establish a Legacy Fund to create a lasting footprint for the town’s future generations with the help of the Central Florida Community Foundation. 

The fund is to be used for town residents to utilize for grants intended to spearhead the way for engagement for outreach work in the local community.

“We don’t want to give something to the town that puts more work on their plate, which is why we are using the Central Florida Community Foundation,” Allen said. “What we do with the money from Wine & Dine right now is it usually comes in and it goes right back out the door, but we want to have a lasting footprint. I think it really could be great if our kids are managing this fund and doing great work in the committee 10, 20, 30 years down the road. That’s what this type of fund can do if you manage it correctly and maintain its vision. 

“We’re doing this to try and encourage engagement, which is what the Wine & Dine Committee has always promoted with Wine & Dine,” Allen said. “It’s not just an event, it’s what we do with the money after the event. We want to give something back to the town.”

The Town Council voted to further develop the concept of the Legacy Fund. More information will be announced on the fund as the Centennial Celebration approaches. 

ITEMS TABLED FOLLOWING CONFLICT

Also at the meeting, two items were tabled following back-and-forth discussion between council members. 

The first was regarding the Third Avenue and Magnolia Street Bessie Drainage - Phase II Subrecipient agreement with the Florida Department of Emergency Management. 

Under the grant process for FDEM, the town was awarded a grant for the much-needed drainage improvements for the Bessie Basin area. 

The staff report in the council’s agenda states the construction scope of work would include upgrading the existing roadway and drainage system by grading the existing dirt road and installing an enhanced stormwater system. The proposed stormwater system includes improving the drainage collection and conveyance with roadside swales, concrete gutters and a stormwater piping system. Additionally, runoff storage shall be increased utilizing a new rain garden and retention areas. 

Council Member Brandi Haines said several residents who would be affected by the project have expressed concerns.

“Whatever the final plans were that were submitted to FEMA … there were some concerns because in the written scope of the work it does not mention that the public potable water is going to be installed,” she said. “It also had said things in there that we hadn’t seen before, including the erosion matting and the sodded areas for the swales. In all the workshops it was discussed that the road was going to be raised to what it was historically and then swales on the other side after the road was crowned, and the water would flow into the existing swales. In the scope of work as it’s written, it says that they’re excavating six inches down and replacing it with six inches paver based … that’s a very, very deep roadway. If it’s only six inches, the concern is how far are we lowering the right-of-way next to these properties, because that doesn’t match what was discussed at every public workshop.”

Town Manager Robert Smith said the town is hoping to obtain additional money for the potable water at the same time, but the town currently does not have the funds to do so. Therefore, the town currently is focused on completing the storm water projects and getting them funded and will attempt to get the funding for the potable water after.

Haines requested to table the item until the next Town Council meeting when more information is available.

“The whole entire project was always designed around having that stormwater control for the water runoff that’s coming from Oakdale (Street), she said. “That’s the entire reason that the culvert now is going to cross from the northwest corner to the northeast corner, but if we’re not going to be collecting the water that’s then going to go through that culvert, it doesn’t make logical sense. I don’t see how the project can function if the whole project isn’t built as a whole. … It feels like a lot of changes. … I’m not comfortable moving forward until we have some answers on some of this.”

Smith said from his understanding the design presented to the Town Council has not changed, and there are a lot of moving pieces associated with the project, including increases in costs over time. 

“Potable water was very important to us,” resident Nancy Bardoe said. “It’s been a long process … so I’m opposed if we don’t get water at the same time, just bottom line. The way the scope and sequence reads, it says they’re going to grade the work and tie the site back to the existing conditions. If you look at our road right now, we’re easily two feet below, and you’re going to take six inches more of that? My understanding was in the design that our road was going to go back to the way it was in the ’80s, and I’m not seeing that in this project at all. … It’s the terminology of this that has really been very confusing and not at all what we’ve dialogued about for the past few years.”

“In a perfect world, we do it all at once, absolutely positively,” Mayor Jim O’Brien said. “We’re reliant upon outside funding streams to do some of these things and make these improvements.”

The design concept for Town Hall, including the stand-alone bathroom with a family restroom, also was tabled following concern from Haines. 

During the previous Town Council workshop, council members directed staff to incorporate a family restroom into the exterior restroom design and return for public review, comments and approval. Staff was seeking approval to proceed with Phase One construction plans, after which the project will be put out to bid. 

“I’m not going to be popular with the staff or council tonight, but I’m probably going to be pretty popular with the residents of the town,” Haines said. “We were supposed to have a Town Square design charrette that got postponed because of Hurricane Helene that never got rescheduled, so we still have not had public input about the Town Square for this design. I have spoken with three former council members, as well as people who have told me on the Historic Preservation Board that they have been waiting for this charrette to give their input on the design of Town Hall. I do not think that we should be moving forward with approving this design without public input.

“Everyone always thinks I’m pointing fingers; it’s not personal,” she said. “I’m here to represent the residents, and whether everybody agrees or doesn’t agree, I do that to the best of my ability.”

Smith said the charette is for Town Square and has nothing to do with Town Hall. 

“I think people get upset, because when you say something like that it makes it sound like we’re working against you and working against the residents, and that you’re the only one working for the residents,” O’Brien said. “I have to say that it’s offensive. If you could just share your input and your ideas, just like the rest of us, that would be fantastic. I want to hear it, but I don’t need the extra kick.”

“It’s offensive to me when I come and I tell what a resident has said at a meeting and get told that it’s my personal opinion and that people are, quote unquote, at past workshops ‘appalled’ at what I’ve said when I’m speaking almost verbatim what was written to me in emails from a resident,” Haines said. 

Council Member Tom Stroup said although he knows the charrette was not specifically about Town Hall, he also was under the impression the charrette would include conversations about town center, which also would include the bathrooms.

 

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Annabelle Sikes

News Editor Annabelle Sikes was born in Boca Raton and moved to Orlando in 2018 to attend the University of Central Florida. She graduated from UCF in May 2021 with a bachelor’s degree in journalism and a minor in sociology. Her past journalism experiences include serving as a web producer at the Orlando Sentinel, a reporter at The Community Paper, managing editor for NSM Today, digital manager at Centric Magazine and as an intern for the Orlando Weekly.

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