On the evening of September 3, Windermere's Town Council sat at Town Hall for its first hearing on the coming year's budget. Council Member Tom Stroup asked to put Christmas lights back into it. The minutes record his suggestion that donations could help cover the cost, followed by a discussion of "holiday lights, Light Up Windermere, Food Truck nights, committee funding, and needs not wants."
Six weeks later the Town posted that Light Up Windermere is returning on Friday, November 20. The other event in that discussion did not come back. The Food Truck Nights page now carries a banner that reads "suspended until further notice." Taken together, the two outcomes show how this fall's downtown calendar was decided. The council told staff to find the money for one town-funded tradition. Most of what remains is hosted by civic groups.
How Both Events Ended Up on the Same Cut List
The sorting began at a budget workshop on Tuesday, July 28. As West Orange Times & Observer reported, Town Manager Robert Smith brought the council a list of events and projects that could be cut or deferred if Amendment 3 passes on November 3. Food Truck Nights and Light Up Windermere were both on it. In that same reporting, Smith explained the line he was drawing:
"Quality of life is one thing, the level of service is another. Quality of life would be having those community events, having lights, Halloween stuff, nice banners. The levels of service would be making sure our roads are in proper condition, making sure the stormwater is working, making sure the police are out protecting everybody."
The figures behind that line are small by county standards but large for a town this size. The Observer reported that about 41% of Windermere's homes, roughly 900, fall under the measure's homestead exemption. Smith estimated the town would lose about $350,000 in the first year if it passes and more than $650,000 in the second. The proposed cuts also took town decorations from $35,000 to $15,000 and signage from $44,000 to $5,000.
The official ballot summary from the Florida Division of Elections says Amendment 3 would raise the homestead exemption for all non-school taxes to $150,000 in 2027 and $250,000 in 2028. It would also cut the annual cap on assessment increases for non-homestead property from 10% to 5%, and it would take effect January 1, 2027. Central Florida Public Media notes that it needs at least 60% of the vote. This post publishes before the vote, so the outcome is not yet known. The summary here is general information and not tax or legal advice, and anyone weighing how the measure applies to their own property should consult a qualified professional.
By the September 3 hearing, the Town had prepared two versions of the budget, a standard one and one with 10% reductions. Light Up Windermere and Food Truck Night started that night with the same status. They ended up in different places because of how the council chose to account for them.
The Council Pulled the Two Events Apart
The two events had been tied together in practice. According to the Observer's September 22 account, Food Truck Night usually coincided with Light Up Windermere. Council Member CT Allen asked that they be separated. "I want Light Up Windermere to be a separate line item," she said, adding that the town could drop the monthly Food Truck Nights and still have food trucks at the holiday event.
Stroup argued for the older traditions. "I think we can cut smaller item projects in order to keep our town events for our residents," he said, as quoted in the same article. The council directed staff to put Light Up funding back into the budget, and Smith told the council the cost of hosting Light Up could be absorbed into the current budget. Part of the reason is that Family Church of Windermere typically provides the activities in front of Town Hall, and White Swan Academy performs indoors and outdoors, both at no charge.
The lights themselves were a separate decision, and they came back with a cap. On September 8 the council voted 4–1 to let staff spend up to $25,000, with Council Member Brandi Haines voting no. The quotes behind that cap came from Public Works Director Tonya Elliott-Moore.
| Holiday lighting option | Cost |
|---|---|
| Last year's Humbug Holiday Lights contract: install, takedown, maintenance | $35,955.27 |
| Humbug quote for a setup similar to last year | About $35,000 |
| Humbug quote, reduced scope around Town Square | $24,997 |
| Second company, full quote | $49,000 |
| Council authorization, September 8 | Up to $25,000 |
The cap is $3 above Humbug's quote for lighting only the Town Square area, and well below last year's contract. The Town has not announced a final scope. Based on the numbers, though, the lights on November 20 will likely cover less of downtown than they did last December. Mayor Andy Williams told the council that residents have offered to contribute to holiday festivities. He said any contractor needed "some sort of resume to look at."
What November 20 Looks Like So Far
The Town's October 12 announcement promises "an evening of food, live performances, and holiday festivities" and asks residents to stay tuned for details. It has not yet announced a venue, hours or performers. Here is what is confirmed for 2026, followed by what happened in 2025:
- Confirmed for 2026: Friday, November 20, with food, live performances and holiday festivities. Lighting is funded up to $25,000.
- What 2025 looked like: The event was held Friday, November 21, outside Town Hall. Family Church choirs sang, White Swan Academy ballerinas performed, food trucks served, a DJ played, and there were glow-in-the-dark bubbles. The downtown holiday lights were switched on at about 7:15 p.m., according to the Observer's photo coverage.
- Possible link to food trucks: Allen's suggestion keeps the door open for trucks at Light Up even while the monthly series is paused. The Town has not confirmed any.
Treat the 2025 program as a guide to the evening, not a schedule. The lighting moment will depend on what the $25,000 buys.
The Fourth Friday Has No Event
Food Truck Night was a monthly fixture. The Town describes it as a fourth-Friday event from 5:30 to 9:30 p.m., usually with 15 to 20 trucks, and paused during June, July and August. This summer the Town made an exception. A July 24 Summer Special brought back the trucks from a canceled April night, including Grandma's BBQ and Smoothie Express. The October 23 Halloween Special is now listed on the Town calendar as "Canceled Until Further Notice."
That leaves a gap in the Friday rhythm we described when the Main Street corner reopened this summer, with the morning Farmers Market at one end and Food Truck Night at the other. The suspension also affects groups beyond the people who came for dinner. As the Observer reported, Haines pointed out that the Historic Preservation Board receives part of its funding from Food Truck Night proceeds. She also questioned why the cuts fell on committees instead of being spread 10% across the board.
Haines and Stroup both said they had heard from residents asking for the series back. Haines said several parents of school-age children told her they did not care whether there was a DJ or a band. One resident suggested bringing an approved playlist to play on a speaker. Stroup asked for a future council discussion. Williams said the council should first see "hard numbers" on cost and staff time. As of late October, no return date has been set.
Who Hosts the Rest of the Season
The town has already used outside sponsors to keep at least one event going. Smith's July plan kept the Easter Egg Hunt Extravaganza by having the Windermere Police Department Foundation fund and organize it. Most of the dates on the calendar between now and February are run by civic organizations:
- Saturday, October 31, 8 a.m. to noon: Sleep in Heavenly Peace Bunk Bed Build at Town Square Park, sponsored by the Windermere Police Department Foundation. The Town is asking for volunteers and new twin-size bedding.
- Fridays, 9 a.m. to 1:30 p.m.: Windermere Farmers Market at Town Square Park, 520 Main Street. The next date on the Town calendar is October 30.
- Wednesday, November 11, 10 a.m.: Veterans Day Observance at Town Hall, hosted by the Rotary Club of Windermere.
- Wednesday, November 11, 11 a.m.: Smiles for Seniors at Town Hall. The Windermere Legacy Fund and the Rotary Club are packing gift bags for Meals on Wheels to deliver.
- Friday, November 20: Light Up Windermere, the town-funded event on this list.
- Saturday, February 6, 2027, 6 p.m.: Windermere Wine & Dine at Town Hall, hosted by the West Orange Foundation. The Observer reported tickets at $175 and dozens of participating restaurants.
Main Street is also getting a new daily stop. Penelope's Coffee is preparing a café at 507 Main St. It plans to serve Orlando-based Lineage Coffee along with baked goods, and its opening is expected sometime this fall. No exact date has been announced.
The November 3 vote reaches past the holidays. Smith told the council the town may defer some capital and infrastructure projects until after the vote and the 2027 and 2028 property values. The work slated for Fiscal Year 2026-2027 includes West Second Avenue water, road and stormwater improvements, stormwater projects in the Bessie and Butler basins, and improvements at the Windermere Road and Main Street intersection.
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