Light Up Windermere Almost Didn't Make the Budget. Here's What's Still On for November 20

"The community involvement and the community events are important to our community, and I think in this case, we need to do all we can within the budget to continue to maintain those events," Council Member Tom Stroup said at Windermere's first budget hearing on September 3, according to the West Orange Times & Observer.

He was talking about Light Up Windermere. About five weeks earlier, the event had been proposed for elimination or suspension. It is now on the town calendar for Friday, November 20, from 5:30 to 9:30 p.m. at Windermere Town Square. Council decided which parts of the evening were worth keeping, and that decision shapes how much money is set aside for lights, who usually performs, and why food trucks are in the event's title.

How a Holiday Tradition Landed on the Cut List

Light Up Windermere first came up for cuts at a budget workshop on Tuesday, July 28. It was one of two town-sponsored events proposed for elimination or suspension. The town was preparing for cuts it would have to make if Amendment 3 passed in November. The Florida Division of Elections summary of Amendment 3 describes three changes. It would raise the homestead exemption for non-school taxes to $150,000 in 2027 and $250,000 in 2028. It would lower the cap on yearly assessment increases for non-homestead property from 10% to 5%. It would also limit how counties and municipalities can use property taxes.

Town Manager Robert Smith told council the cuts came down to needs versus wants. "$5,000 here, $10,000 here, $35,000 here, it all adds up to that 10%," he said, according to the Observer. Other lines shrank as well. Sidewalk repair and construction dropped from $100,000 to $20,000, and signage dropped from $44,000 to $5,000.

On Wednesday, September 16, council unanimously adopted a Fiscal Year 2026-27 budget of $12,464,394.17 with an operating millage of 3.7425. By then, staff had been told to put Light Up Windermere back in. Smith said the town could absorb the cost of hosting the event within the current budget.

Hosting the evening and lighting the town are two separate costs, though, and the budget treated them separately.

The Lights Are the Part That Got Smaller

The FY2027 budget proposal had removed the holiday lights entirely. Stroup asked council to consider funding them again. At its Tuesday, September 8 meeting, council voted 4-1 to let staff spend up to $25,000 on holiday lights. Here is how that cap compares with last year's spending and this fall's quotes:

The $25,000 cap is $3 above Humbug's reduced-scope quote and about $11,000 below what lighting at last year's scale would cost. Public Works Director Tonya Elliott-Moore described the reduced scope as lights for the area around Town Square. The town describes Town Square Park as the block from Main Street to Forest Street, between West 5th and West 6th avenues.

A cap sized to that quote points toward lights for the block where the event takes place. Last year, the Observer's photo coverage of Light Up Windermere 2025 described new downtown holiday lights switched on at about 7:15 p.m. The reduced scope Humbug priced would cover a smaller area, centered on the square where the crowd gathers.

Mayor Andy Williams said he had been talking with residents who are willing to help pay for holiday festivities. He also wanted to be careful about who gets hired. "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," he said, according to the Observer.

What the Evening Is Built On

Lights are the expensive part of the event. Much of the rest has been free to the town for years. Smith told council that Family Church of Windermere usually provides the activities in front of Town Hall and White Swan Academy performs indoors and outdoors, and that both do it for free. Last year, Family Church's choir sang and White Swan Academy's ballerinas performed, alongside food trucks, a DJ and bubbles.

Food trucks are the other half of this story. Food Truck Nights were the second town-sponsored event proposed for elimination or postponement, and they usually took place on the same night as Light Up Windermere. Council Member CT Allen asked that the two be kept apart in the budget:

"I'd like to make sure we protect Light Up Windermere, whether it's a food truck or whatever, I want to protect that event environment. ... I want Light Up Windermere to be a separate line item."

Allen said the town could still drop Food Truck Nights and bring food trucks to Light Up Windermere, so residents would get the same experience as in past years. The November 20 calendar listing reflects that approach. Its title is "Food Truck Night WPD Foundation: Light Up Windermere!"

The recurring Food Truck Night series did not get the same protection. Haines and Stroup both said residents had asked for Food Truck Nights to continue. Haines said parents of school-age children had told her they did not care whether there was a DJ or a band, because they simply wanted to gather at a community event. Williams asked for "hard numbers" on cost and staff time before any discussion of bringing the series back. "The bottom line is, we still have to cut something else to bring it back," he said, according to the Observer. Those evenings also supported a town committee. Food Truck Night proceeds help fund the Historic Preservation Board.

As it stands, the November 20 listing carries both the Light Up name and the Food Truck Night name, and council has authorized up to $25,000 for holiday lights.

Getting to Town Square Without Circling for Parking

If the event fills downtown the way it has before, getting there will be easier than last year for some residents. The Ward Trail and its pedestrian bridge partly opened on August 6. The project includes about half a mile of shared-use trail, drainage improvements, landscaping and the bridge, which pedestrians, cyclists and people in golf carts can all use, according to the Observer's report on the opening. The bridge crosses the canal. The town's announcement said final pathway sections, landscaping and finishing touches would continue through the fall, with a full grand opening planned for fall or winter.

The town's Ward Trail project page describes Phase I as running from Town Center to Windermere Elementary. Earlier council project summaries placed it between North Avenue and Park Avenue, along railroad right-of-way the town acquired. Funding included a $760,000 federal earmark, $1,000,000 in state appropriations and American Rescue Plan Act money.

The trail is open to golf carts, but street driving falls under the town's golf cart rules, which cite Florida Statute 316.212 and Town Ordinance 2023-04. Under those rules:

• Carts may only be driven on roads shown on the town's Golf Cart District Map that have posted speed limits of 30 mph or less.
• Golf carts are not titled or registered, and they do not require PIP/PDL insurance.
• Operators must be at least 18 or hold a valid driver's license or learner's permit.

This is general information about the town's rules, not legal or insurance advice. If you have questions about your own cart or coverage, check with the town or your insurance professional before November 20.

The Rest of November on Main Street

Three days after the lighting, Town Hall hosts Game Night on Monday, November 23, from 5:30 to 9 p.m. at 520 Main St. It is potluck-style and bring-your-own-game, so guests bring their own games and snacks.

A few doors down at 507 Main St. is Penelope's Coffee, from Windermere residents Leti Freitas and Joe Harris. The Observer reported in October that the café plans to serve Orlando's Lineage Coffee and freshly baked goods. "Our hope is that Penelope's becomes your go-to cozy space where you can unwind, take a quick lunch break or catch up with an old friend," the owners wrote on Instagram, as reported by the Observer.

Last year, the town scheduled Holiday Hoopla to begin on Friday, December 5, at 6 p.m. The 43rd Hoopla had Santa, food trucks, a petting zoo, rock climbing and arts and crafts, according to the Observer's coverage.

At CC Luxury Group, we follow how town budgets shape everyday life in Windermere, from the lights on Town Square to the trail that connects it to nearby neighborhoods. If you are thinking about how decisions like these affect a home near Main Street or along the Ward Trail, schedule a complimentary luxury consultation with Crystal Canina.