Light Up Windermere Survived the Budget Cuts. What Does This Year's Town Square Look Like?

Windermere Public Works Director Tonya Elliott-Moore went to Humbug Holiday Lights this fall with two questions. The first was the cost of a display like last year's. The answer stayed around $35,000. The second was the cost of lighting only the area around Town Square. That quote came back at $24,997.

On September 8, Town Council voted 4-1 to let staff spend up to $25,000 on holiday lights. Council member Brandi Haines cast the dissenting vote. The cap sits $3 above the smaller quote. So when Light Up Windermere returns on Friday, November 20, the lights will likely cover less ground than last year. The rest of the evening is a different story. Most of it never depended on the town's budget.

That split runs through Windermere's whole holiday season. The items the town pays for went through budget review. The pieces run by neighbors, churches and civic clubs didn't need to.

Where the cuts started

Over the summer, Windermere wrote two budgets for fiscal year 2027. One was a regular budget. The other cut 10% in case voters approved the property tax amendment on the November 3 ballot. According to Ballotpedia's summary of Florida Amendment 3, the measure raises the homestead exemption for non-school property taxes to $150,000 in 2027 and $250,000 in 2028. It also lowers the cap on yearly assessment increases for non-homestead property from 10% to 5%, and it limits what local property tax money can be spent on.

At a July 28 workshop, two town-sponsored events were proposed for elimination or suspension: Light Up Windermere and Food Truck Nights. The holiday lights were dropped from the proposed budget entirely. On September 16, council unanimously adopted a $12,464,394.17 budget with an operating millage of 3.7425. Town Manager Robert Smith said sidewalk extensions would wait for the amendment's outcome. He also said the budget could be adjusted later.

What the lighting money buys this year

Council member Tom Stroup pushed to restore the event and its lights at the first budget hearing on September 3. The West Orange Times & Observer reported his comment that "we can cut smaller item projects in order to keep our town events for our residents." The September hearing minutes show he also raised donations as a way to offset the cost.

Here is how the options stacked up, as the Observer reported in September:

The second company was still working on a reduced-scope quote when the Observer published. The town has not yet released a final vendor or a street-by-street lighting plan. For now, the reliable expectation is a smaller display centered on Town Square. Mayor Andy Williams said he had been talking with residents willing to contribute toward holiday costs. That leaves room for private money to add to the display.

Why the evening itself was easy to save

The lights cost money, but the rest of Light Up Windermere mostly doesn't. Smith told council that Family Church of Windermere usually runs the activities in front of Town Hall. White Swan Academy usually performs indoors and outdoors. Both do it for free, and Smith said the town could absorb the cost of hosting the event within the current budget. Neither group's 2026 role has been announced yet. Still, that arrangement explains why the event survived when its lighting line item did not.

The town's own notice promises "an evening of food, live performances, and holiday festivities" on November 20. A local community event listing gives the details: 5:30 to 9:30 p.m. at Windermere Town Square Park, 520 Main St., with the lights switching on at 7 p.m.

For an evening on Main Street, plan around those times:

1. Arrive after 5:30 p.m., when the event opens at Town Square Park.
2. Expect the performances and Family Church's activities, if they follow past years, near Town Hall.
3. Be on the square by 7 p.m. for the lights-on moment.
4. Make your last stop by 9:30 p.m., when the evening wraps up.

Food trucks, the line item still in question

Food Truck Nights is the one budget piece still unsettled. The event usually took place the same night as Light Up Windermere. Council member CT Allen said the town could drop the standalone Food Truck Nights and still bring food trucks to Light Up. She asked for Light Up to be "a separate line item." Haines and Stroup both said they had heard from residents asking for Food Truck Nights to continue.

The money involved goes beyond dinner. Haines pointed out that part of the Historic Preservation Board's funding comes from Food Truck Nights proceeds. She objected that the town's committees were taking cuts while other items were being restored. The town's Food Truck Nights page still describes a recurring fourth-Friday event and tells visitors to check the current month's details. The fourth Friday of November is the 27th, the day after Thanksgiving. Check the page before planning around it.

The rest of November, run by neighbors

Once you look past the light display, most of Windermere's November calendar is organized by clubs, foundations and volunteers rather than paid for by the town. Here are the dates for the month ahead:

• Fridays, November 6, 13, 20 and 27: The Town Farmers Market runs 9 a.m. to 1:30 p.m., weather permitting, at Town Square Park on Main Street between Fifth and Sixth Avenues. On November 20, the market and Light Up share the same park, at different hours.
• Mondays, November 9 and 23: Town of Windermere Game Night meets at Town Hall on the second and fourth Mondays. Bring a game and snacks.
• Wednesday, November 11, 10 a.m.: The Rotary Club of Windermere hosts its annual Veterans Day observance at Town Hall.
• After the November 11 ceremony: The Windermere Legacy Fund and the Rotary Club of Windermere need volunteers for Smiles for Seniors. Volunteers pack gift bags with essentials and holiday treats, and Meals on Wheels delivers them to seniors. Sign-up is on the town's news feed, or you can email [email protected].

Other fall events followed the same pattern. The Windermere Historic Preservation Board held its second annual Pumpkin Carving Potluck on October 25. The Windermere Police Department Foundation's Sleep in Heavenly Peace bunk bed build took donations of new twin bedding at the Windermere PD lobby and at Flippers Pizza Co. on Old Brick Road. Looking ahead, the West Orange Foundation's Windermere Wine & Dine returns Saturday, February 6, 2027. Tickets went on sale October 24.

The project that was already paid for

Ward Trail is one town project the budget debate didn't touch, because it was already built. In August, the town opened parts of the trail and its pedestrian bridge over the canal. The project covers about half a mile of shared-use trail, plus drainage improvements and landscaping. The bridge is open to pedestrians, bicycles and golf carts. The town's announcement quoted Mayor Williams calling it "a safer connection between our neighborhoods, parks, and school."

Finishing work has continued through the fall. Crews put up signs along Ward Trail and Centennial Bridge on October 27. The town has said an official grand opening will come in the fall or winter season but hasn't set a date.

Main Street on Light Up night

The square will have more open storefronts nearby than it did a year ago. Fresco Pizzeria is now open at 527 Main St., according to its Windermere page. A few doors away, Penelope's Coffee is preparing a café at 507 Main St. The West Orange Times & Observer reported on October 2 that renovations were nearly finished and a fall opening was expected. As of mid-October, the café had not announced an opening date.

Council discussed sponsors and donations when it approved the lighting cap, so private contributions could still add to this year's display.

The team at Bobby Baldor keeps up with Windermere's council decisions and its community calendar. If you have questions about how Town Square, Main Street or the Ward Trail project relate to a home you own or are considering, Contact Us. We're happy to share what we know.