"Quality of life would be having those community events, having lights, Halloween stuff, nice banners." Windermere Town Manager Robert Smith said that at a July 28 budget workshop, as reported by the West Orange Times & Observer. He set those events against "levels of service," which he described as roads, stormwater and police. The council was planning for a possible hit to town revenue if the proposed property tax amendment on the Nov. 3 statewide ballot passes. Smith estimated the hit at about $350,000 in the first year and more than $650,000 in the second.
This fall's calendar shows what came of that line. Most of the town's traditions are still on, and a church, a police foundation, a volunteer board or a local business now carries much of the work. Food Truck Nights, a series the Town scheduled and staffed itself, has stopped.
The Two Events Put on the Table in July
Smith's list of town-sponsored events that could be cut or suspended had two items on it: Food Truck Nights and Light Up Windermere. A third tradition changed hands that same night. The Easter Egg Hunt Extravaganza will continue, but the Windermere Police Department Foundation will now fund and organize it.
Smith framed the question the council would have to answer in the Observer's account:
"It's those (events) that taxpayers look at and say, 'Is this necessary? Is this needed? Was it just something we want?'"
He also said any cuts could be added back depending on cash flow. Within six weeks, one of the two events was back.
How Light Up Windermere Got Back In
At the Sept. 3 tentative budget hearing, Council Member Tom Stroup argued for restoring the holiday lights. He suggested donations could help cover the cost, and the hearing minutes in the Town Council's Oct. 13 agenda packet record a discussion of holiday lights, Light Up Windermere, Food Truck Nights and "needs not wants." The West Orange Times & Observer quoted him: "I think we can cut smaller item projects in order to keep our town events for our residents."
Light Up survived largely because so little of it ran through the Town's books. Smith told the council that Family Church of Windermere usually provides the activities in front of Town Hall and White Swan Academy provides indoor and outdoor performances, all at no charge. He said hosting the event could be absorbed into the current budget.
The lights cost real money. Last year the Town paid $35,955.27 to Humbug Holiday Lights to install, maintain and take down the display. When Public Works Director Tonya Elliott-Moore asked for this year's price, the same scope still came in around $35,000. A reduced scope covering the area around Town Square was quoted at $24,997. A second company quoted $49,000 for the full job. On Sept. 8, the council voted 4-1 to spend up to $25,000 on holiday lights, with Council Member Brandi Haines dissenting. That ceiling sits about $3 above the reduced Town Square quote, so this December's lights will likely cover a smaller area than last year's. Mayor Andy Williams said he had been talking with residents willing to contribute toward holiday costs.
On Oct. 12 the Town confirmed that Light Up Windermere returns Friday, Nov. 20, with food, live performances and holiday festivities. Start time and other details are still to come.
Food Truck Night Ran Through Town Hall
The Town sets the schedule and takes vendor applications. A Food Truck/Farmers Market Selection Committee approves each truck, and the Town charges $150 per truck per event. Local businesses have sponsored some editions, but the scheduling and vendor work sat with Town staff and the committee. The Food Truck Nights page now says the series is suspended "until further notice." The Halloween edition planned for Friday, Oct. 23, carries the same label on the Town calendar.
The two events were tied together. According to the Observer, a Food Truck Night usually coincided with Light Up. Council Member CT Allen suggested the Town could drop the standalone series and still bring food trucks to Light Up, and she asked that Light Up be budgeted as its own line item. No vendor lineup has been announced for Nov. 20.
The pause also affects groups beyond the trucks. Haines raised the concern that the cuts fell on events that help fund the Historic Preservation Board and the Windermere Tree Board. The Historic Preservation Board receives some of its funding from Food Truck Night proceeds. The council adopted the $12,464,394.17 budget for FY 2026-27 unanimously on Sept. 16, keeping the millage rate at 3.7425. At that hearing, a resident spoke about food trucks, holiday events and keeping community events going.
The Beer Festival Stopped for Its Own Reason
The Craft Beer Festival planned for Oct. 17 was also canceled, but the budget was not the cause. The Town announced the cancellation on Sept. 22 and promised full refunds to ticket holders and sponsors. Organizers told the West Orange Times & Observer that "we have faced challenges that have made it difficult to assemble the type of brewery participation necessary to deliver the festival at the level we believe it deserves." They called it "a pause while we figure out what's next."
On the original date, a local business held its own event. Windermere Brewing Co. and King of Pops put on a first-ever Backup Beer Fest, with breweries from around Orlando set up in the brewery's backyard. A tall cup stood on the lawn as a trophy for the most popular beer, to be held by the winning brewery until the next event. King of Pops owner Mike Butler called it a "rodeo of supporting small businesses," the Observer reported.
Who Is Carrying the Rest of the Season
The schedule from here, with the group behind each event:
| Date | Event | Who runs it | Details |
|---|---|---|---|
| Saturday, Oct. 24 | Halloween Hayride & Costume Parade | Town of Windermere | 9:30 a.m. to noon |
| Sunday, Oct. 25 | Pumpkin Carving Potluck | Historic Preservation Board | 4 to 6 p.m. at Town Hall, RSVP requested |
| Saturday, Oct. 31 | Bunk-bed build | Windermere Police Department Foundation with Sleep in Heavenly Peace | 8 a.m. to noon, Town Square Park |
| Fridays | Farmers market | Town of Windermere | 9 a.m. to 1:30 p.m., Town Square Park, weather permitting |
| Friday, Nov. 20 | Light Up Windermere | Town, with Family Church of Windermere and White Swan Academy in past years | Details to come |
The hayride is the Town's annual parade, and the Town's post puts the start at Town Hall. Its event listing names Town Square Park, so check the Town's page before you head out.
The potluck is free for residents and guests. Bring a pumpkin, carving tools and a dish to share. For the Halloween morning bunk-bed build, organizers are asking for volunteers and donations of new twin bedding. The farmers market sells produce, seafood, baked goods, coffee, flowers and handmade goods. It is at capacity and not taking new vendors. The Town calendar runs the market through Dec. 18.
What Opens on Main Street While the Calendar Shrinks
Some new things are arriving downtown this fall. Penelope's Coffee is set to open at 507 Main St., a few doors from Town Square. Owners Leti Freitas and Joe Harris plan to serve Lineage Coffee and baked goods. As of the Observer's Oct. 2 report, renovations were nearly complete and no opening date had been announced.
Parts of the Ward Trail and its new bridge over the canal opened before the school year began. The route is about half a mile and open to people on foot, bikes and golf carts, according to the Town's update. Finishing work continues through fall, and a full grand opening is planned for fall or winter. On Sept. 8 the council voted 5-0 to name the bridge the Centennial Bridge, after the logo designed for the town's centennial celebrations.
If you launch from the town boat ramp, renewals of the annual ramp pass are on hold until Dec. 1. Current key and code holders keep access in the meantime at no extra charge. At a Sept. 22 workshop, the council left the annual pass at $35.
The schedule could change again after Nov. 3. In July, Smith said that if property values keep rising, it could take the town about three or four years to get back to where it is now. He also said the cuts can be reversed if cash flow allows. Whatever the outcome, the next Town Council agenda will show whether Food Truck Nights return to the fourth-Friday schedule.
Our team at Core4 Group keeps track of changes like these in Windermere, from Main Street openings to the holiday calendar. If you'd like to talk through what's happening near your home or a home you're considering, we'd be glad to help. Book a Consultation.
