Light Up Windermere happens on Friday, Nov. 20, at Town Square. This summer it was on a short list of events the town might drop. Council members put it back in the budget, but with a lower cap on lights. The cap they approved matches a quote for lighting the area around Town Square, well below what last year's display cost. The new Ward Trail and its golf-cart-width bridge now connect neighborhoods north of the canal to that same square.
How a Holiday Tradition Ended Up on the Cut List
On July 28, Windermere held a budget workshop to plan for cuts in case Amendment 3, the statewide property-tax measure, passed in November. Two town-sponsored events were proposed for elimination or suspension: Light Up Windermere and Food Truck Nights.
The amendment passed. Bay News 9 reported that it received 62% of the vote, above the 60% it needed. It raises the homestead exemption for non-school property taxes to $150,000 in 2027 and $250,000 in 2028. The same report said local governments don't expect property-tax revenue to drop much until fall 2027, with a much bigger reduction expected in 2028. That means this holiday season is the first one Windermere budgeted with those cuts already in mind.
Council Member Tom Stroup was the one who argued at the first budget hearing on Sept. 3 that the event should come back. As the West Orange Times & Observer reported, he said "we need to do all we can within the budget to continue to maintain those events, especially some of the more historic ones we've had (for) quite a while," and added that the town could "cut smaller item projects in order to keep our town events for our residents." Town Manager Robert Smith said the town could cover the cost of hosting the event within its existing budget.
The lights were a separate question. The proposal for Fiscal Year 2027 had removed them completely.
The Number Behind the Cap
Public Works Director Tonya Elliott-Moore got prices for two options. One was for lights similar to last year's. The other was a reduced scope covering the area around Town Square. On Sept. 8, the council voted 4-1 to let staff spend up to $25,000 on holiday lights.
Option | Cost |
|---|---|
Last year's Humbug Holiday Lights contract: install, takedown and maintenance | $35,955.27 |
Humbug quote for lights similar to last year's | About $35,000 |
Second company's quote | $49,000 |
Humbug quote for the reduced scope around Town Square | $24,997 |
Spending cap approved by council on Sept. 8 | Up to $25,000 |
The cap is $3 above the Town Square quote and almost $11,000 less than last year's contract. The council's limit lands right at the quoted price of lighting the heart of downtown. For comparison, the Fiscal Year 2026-27 budget the council adopted on Sept. 16 totals $12,464,394.17, with an operating millage of 3.7425. The lights are capped at about two-tenths of one percent of that budget.
Mayor Andy Williams said he had been talking with residents who were willing to help pay for holiday festivities. He also said he wanted the job done by an experienced company. He told the Observer, "the last thing I want to do is hire two guys in a truck and pay them $15,000, and we get $5,000 worth of work."
What Fills the Square on Nov. 20
Whatever the lights budget, the evening's program depends on two local groups. Smith told council that Family Church of Windermere usually runs the activities in front of Town Hall, and White Swan Academy performs indoors and outdoors, both at no charge. Council Member CT Allen asked that Light Up Windermere get its own line item, separate from the other Food Truck Nights, so food trucks could still come to the holiday event. On the town calendar, the evening is listed as "Food Truck Night WPD Foundation: Light Up Windermere!" from 5:30 to 9:30 p.m. at Windermere Town Square.
The Town of Windermere's event page gives this schedule:
- 5:30 p.m.: Event begins
- 5:30 to 6:15 p.m.: Youth choirs from Family Church and Olympia High School
- 6:15 to 6:45 p.m.: White Swan Nutcracker performance inside Town Hall
- 6:45 to 7:15 p.m.: Family Church adult choir
- 7:15 p.m.: Lights go on
- 7:25 to 9:15 p.m.: Lights, food trucks and a DJ
- 9:30 p.m.: Event ends
Trucks on the town's list include Alaskan Ice Truck, Al's Gelato Dessert Sundaes, Arepa Pela Orlando, Bao Houz, BBQ Brazil Express, Bon Appetit, The Crepe Company, Donuts and Real Espresso, Dio Santo Street Pizzeria, The Hook Orlando, Lee's Famous Cheesesteaks, Monsta Lobsta, Oishiimotto and Smash Brothers.
Nov. 20 is a Friday, the same day as the regular Windermere Farmers Market. The town lists the market from 9 a.m. to 1:30 p.m. at Town Square Park, 520 Main St. The town also notes that the market closes on days when Town offices are closed. On a regular market day, the square will host the market in the morning and the lighting at night.
A New Way to Town Square From North of the Canal
This fall it also became easier to get to Town Square without a car. In August, the town opened parts of the Ward Trail and its new pedestrian bridge. The project includes a shared-use trail, a bridge over the canal, drainage improvements and landscaping. The bridge is built for pedestrians, bicycles and golf carts.
The West Orange Times & Observer described the Phase 1 route as running from North Drive to Park Avenue. It crosses the canal between Lake Down and Lake Butler on a railroad-style bridge 8 feet tall and 14 feet wide, wide enough for two golf carts to pass each other. Smith told the paper that because the old pedestrian bridge was too narrow, people had been taking their golf carts over the road bridge to get to and from downtown. The main purpose of the wider bridge, he said, was to link old downtown Windermere with newer parts of town, so that people north of the canal can reach parks, boat ramps and the town's civic centers.
The plans call for longleaf pines, firebushes, saw palmettos and Sabal palms along the path, with benches and lighting. The town scheduled crews to install signs along the Ward Trail and Centennial Bridge on Tuesday, Oct. 27. The town said final pathway sections, landscaping and other finishing work would continue through the fall, and that a full grand opening is planned for this fall or winter. For Light Up night, households north of the canal can take a golf cart across the Centennial Bridge to Town Square without using the road bridge.
The Weekend Before the Lights
The town's holiday season starts six days before the lighting, in the same building. Windermere's Holiday Extravaganza Art Show is Saturday and Sunday, Nov. 14 and 15, from 10 a.m. to 5 p.m. at Town Hall, 520 Main St. The town lists holiday shopping, local artists, live entertainment, food trucks and family activities. If you're looking for a gift from a local artist, this is the place to find one before the square fills up on the 20th.
Smaller Notes Around Town This Month
Not everything new this month is on Main Street. A few other dates are coming up:
- CAVA at The Grove. The West Orange Times & Observer reported that the Mediterranean chain set Monday, Nov. 9, as its opening date at 4757 The Grove Drive, Suite 100. The menu includes grain and salad bowls, pitas and hummus.
- Boat-ramp and tennis passes. On Sept. 16, the town put renewals of tennis keys and boat-ramp passes on hold until Dec. 1 while council considers fee changes. Current users can keep using their existing keys and codes at no extra charge during the pause. The town's notice is where updates will appear when renewals start again.
- Dirt roads after rain. After heavy rain on Nov. 2, Public Works reported a small washout next to Lake and 5th. The road was still passable, and grading of dirt roads has to wait until conditions dry out.
What the Cap Says About the Calendar Ahead
At the September hearings, budget pressure and community pressure pushed in different directions. Council Member Haines and Council Member Stroup both said residents had asked them to keep Food Truck Nights. Some proceeds from Food Truck Nights also help fund the Historic Preservation Board. This year the council kept the event by capping lights below last year's cost, absorbing the hosting costs into the existing budget, and relying on performances local groups provide for free. The larger revenue changes from Amendment 3 come in fall 2027 and 2028, so the council will make these choices again in next year's budget hearings.
David and Rema have watched Town Square change from season to season, and they're happy to talk about what the town's budget decisions could mean for downtown in the years ahead. Or just say hello by the Town Hall steps when the lights go on at 7:15. If you have questions about Windermere's events, the new trail, or where the town is headed, reach out to the Perras Team and Contact Us anytime.
