Light Up Windermere was on a list of proposed cuts this summer, and Town Council voted it back into the budget in September. The event returns to Town Square Park on Friday, Nov. 20, at 5:30 p.m.
Light Up Windermere is still on, and it looks a lot like it always has. Choirs, ballet and a countdown, then food trucks and a DJ until 9:30. The difference is what's around it. This fall the monthly Food Truck Nights came off the Town calendar, and the lights were funded at a smaller level. So the Nov. 20 event is now doing several jobs that used to be spread out across the year.
How a Holiday Night Ended Up in a Budget Workshop
At a July 28 budget workshop, Town staff proposed eliminating or suspending two town-sponsored events. Those were Light Up Windermere and the Food Truck Nights. The goal was to prepare for cuts if Amendment 3 passed in November, according to the West Orange Times & Observer. The holiday lighting was also taken out of the Fiscal Year 2027 budget proposal.
At the first budget hearing on Sept. 3, Council Member Tom Stroup argued to bring Light Up back. "The community involvement and the community events are important to our community," he said, as reported by the Observer. He added that he would rather cut smaller projects "in order to keep our town events for our residents."
Council Member CT Allen then made the move that shaped this year's calendar. In the past, Food Truck Night usually fell on the same evening as Light Up. Allen asked to separate the two, according to the Observer's coverage:
"The other Food Truck Nights, I don't want them tied together that we either say yes for all Food Truck (Nights) and that incorporates Light Up Windermere. I want Light Up Windermere to be a separate line item."
Town Manager Robert Smith said the event could be absorbed into the current budget. Part of the reason it's affordable is that much of the program costs the Town nothing. Smith said Family Church of Windermere usually provides the activities in front of Town Hall. White Swan Academy performs indoors and outdoors. Both do it for free. Council adopted the FY2026-27 budget unanimously on Sept. 16. The total budget is $12,464,394.17, with an operating millage of 3.7425.
Florida voters approved Amendment 3 on Nov. 3. WUSF reported 61.98 percent yes to 38.02 percent no, with all 5,718 precincts in, in results updated Nov. 6. The measure needed 60 percent to pass.
The Program, Minute by Minute
The Town has posted a timed schedule on its Light Up Windermere page. Everything happens at Town Square Park and Town Hall, 520 Main St.
- 5:30 p.m. The event opens with youth choirs from Family Church and Olympia High School.
- 6:15 to 6:45 p.m. White Swan performs The Nutcracker inside Town Hall.
- 6:45 to 7:15 p.m. The Family Church adult choir performs.
- 7:15 p.m. The lights go on.
- 7:25 to 9:15 p.m. Lights, food trucks and a DJ.
- 9:30 p.m. The event ends.
Two things are new this year. In 2025, the program had Family Church singers and White Swan ballerinas, a countdown at about 7:15 p.m., then a DJ and glow-in-the-dark bubbles. This year adds the Olympia High School youth choirs. It also gives White Swan a set Nutcracker performance indoors. In 2024, the event started at 5 p.m., the lights came on at 7 p.m., and the Orlando Bubble Bus ran from 7 to 9 p.m. The 7:15 countdown has now held for two years.
The Nutcracker runs only 30 minutes, inside Town Hall, and it ends just as the adult choir starts outside. If you want to see both, go in early and step back out at 6:45.
Seventeen Trucks, One Night
On the Town's events calendar, the listing is titled "Food Truck Night WPD Foundation: Light Up Windermere!" with hours of 5:30 to 9:30 p.m. It's the only Food Truck Night on the November calendar. Council said it wanted hard numbers on cost and staff time before discussing whether the monthly series comes back. Mayor Andy Williams pointed out that bringing it back would still mean cutting something else, according to the Observer.
That helps explain why the truck list is so long. Council Members Brandi Haines and Stroup both said residents had been asking them for Food Truck Nights. Haines said parents of school-age children had told her they don't need a DJ or band; they just want a community event to gather at. The Town lists 17 trucks for the night.
- Savory: Arepa Pela Orlando, Bao Houz, BBQ Brazil Express, Bon Appetit, Dio Santo Street Pizzeria, The Hook Orlando, Lee's Famous Cheesesteaks, Monsta Lobsta, Oishiimotto, Pico Bistro, Smash Brothers, Tagliolino Fresh Pasta
- Sweet and snack: Alaskan Ice Truck, Al's Gelato Dessert Sundaes, The Crepe Company, Donuts and Real Espresso, The Pretzel Spot
Since this is the year's one Food Truck Night, expect lines at the trucks during the 7:15 countdown. The choirs at 5:30 are a quieter time to get dinner.
A Smaller Footprint for the Lights
The countdown is the same as before, but the lights it switches on have been scaled back.
In 2025, Windermere spent $35,955.27 on a Humbug Holiday Lights contract to supply, install, maintain and remove the display. The Observer reported that the lights ran up the trunks and out the branches of 25 trees, plus 59 light posts. That contract replaced an older setup. Public Works Director Tonya Elliott-Moore said the Town's own lights had become too old for contractors to install safely.
On Sept. 8, 2026, council voted 4 to 1 to let staff spend up to $25,000 on holiday lights. Haines voted no. Elliott-Moore said Humbug priced last year's scope at about $35,000 again. A smaller scope covering the area around Town square came in at $24,997. A second company quoted $49,000 and was working on a reduced-scope price. Williams said he had been talking with residents willing to help pay for the holiday festivities, per the Observer.
Compared with last year, the spending cap is about $11,000 lower, and the quote that fits under it centers on Town Square. That puts the display right where the 7:15 countdown happens.
What Each Town Event Quietly Pays For
Some of Windermere's town events help pay for the volunteer boards that look after its character.
The Historic Preservation Board gets part of its funding from Food Truck Night proceeds. Smith said that before that money started, the board had to raise its own funds. He said the Windermere Tree Board gets "some good money" from the Windermere Farmers Market. Haines objected that the cuts were landing on events that fund those two boards, according to the Observer.
So the Friday market is more than a place to buy produce. It also helps fund the board that looks after Windermere's trees. That's useful to know before a trip down Main Street.
The Rest of November Around Town Square
The Windermere Farmers Market runs Fridays from 9 a.m. to 1:30 p.m. at Town Square Park, 520 Main St. On Nov. 20, that means the market and Light Up share the same lawn on the same day, with four hours in between.
The Town's posted rule is that the market closes whenever Town offices do. The calendar lists Nov. 26 and 27 as the Thanksgiving holiday, so plan for no market the Friday after Thanksgiving. Nov. 13 and Nov. 20 are the last two market Fridays before the break.
On Monday, Nov. 23, Game Night at Town Hall runs from 5:30 to 9 p.m. It's a casual, bring-your-own-game, potluck-style evening, and the Town lists a TeamReach group for RSVPs on its events calendar.
Main Street also has a new name to watch this season. Penelope's Coffee, a café from Windermere residents Leti Freitas and Joe Harris, has been finishing renovations at 507 Main St. The Observer reported in October that it was expected to open this fall, with Orlando's Lineage Coffee and baked goods on the menu. The owners have said they hope it becomes a spot for "a quick lunch break or catch up with an old friend."
If you're thinking about listing a home near Main Street, the nights when Town Square fills up are the best time to show off your street. Gavin Hatch and the APEX team capture neighborhood moments like Light Up in our listing films, so buyers see how it feels to live there. Start with a Free Home Valuation, and we'll show you how we'd present your home this season.
