On Thursday, Sept. 3, at Windermere's first budget hearing for fiscal year 2027, Council Member Tom Stroup asked to put Light Up Windermere back on the books. In a July 28 workshop, the holiday event had been proposed for elimination or suspension. Its lights had also been taken out of the draft budget. Town leaders were preparing for cuts in case Amendment 3, a property tax reform measure, passed in November.
Stroup's request worked. Food Truck Nights were the other town event on the chopping block, and they are still paused. For anyone in Keenes Pointe who treats downtown Windermere as the default place to spend a holiday evening, that split explains this year's calendar. The town is paying for one big night, at a smaller scale. Most of what surrounds it is being carried by churches, service clubs, a foundation and neighbors who turn up with their own snacks.
One Night, Trimmed to Fit
Light Up Windermere returns Friday, Nov. 20, at Town Square Park, 520 Main St. The town's announcement promises "an evening of food, live performances, and holiday festivities" and says more details are coming closer to the date. The community calendar Windermere Neighbors lists the event as free, running 5:30 to 9:30 p.m., with the lights coming on at 7 p.m. Those times come from a community listing, not the town, so check the Town of Windermere site the week of the event.
The bigger change is the lights. According to the West Orange Times & Observer, last year the town spent $35,955.27 on its contract with Humbug Holiday Lights. That contract covered bringing in the lights, putting them up, taking them down and maintaining them. This year the council capped spending well below that. Here is how the numbers lined up when the vote happened:
- Last year's Humbug contract: $35,955.27
- Humbug's quote to repeat last year's display: about $35,000
- Humbug's quote for a reduced scope around Town Square: $24,997
- A second vendor's quote: $49,000, with a reduced-scope quote still in the works
- What the council authorized on Sept. 8: up to $25,000
The vote was 4-1, with Council Member Brandi Haines opposed. The $25,000 cap sits $3 above Humbug's reduced-scope quote and roughly $11,000 below last year's spending. Humbug described that smaller scope as lighting the area around Town Square. Anyone who remembers how far the display stretched in past seasons should expect it to stay closer to the park this time.
Mayor Andy Williams told the Observer he has been talking with residents willing to help pay for holiday festivities. He also explained why the town is wary of the cheapest bidder: "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."
The Event Itself Was Never the Expensive Part
Town Manager Robert Smith told council that hosting Light Up can be absorbed into the current budget. He explained why in the same meeting. The Family Church of Windermere typically runs the activities in front of Town Hall, and White Swan Academy typically performs indoors and outdoors. Both do it for free.
So the evening that ends up on everyone's camera roll, the choirs and dancers and kids' activities, comes from local groups giving their time. The town pays for the lights. That's why the lights were the line item that got squeezed. Smith was describing how the event typically runs, and the town has said more details are coming as Nov. 20 gets closer. The Windermere Neighbors listing describes "holiday choirs, dancers and live entertainment."
Stroup made the case for keeping it in terms that go beyond one night, according to the Observer's account of the hearing:
"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, especially some of the more historic ones we've had (for) quite a while."
Why Food Truck Night Is the One That Stayed Off
Food Truck Night usually coincided with Light Up. That's why the two were weighed together in July. Council Member CT Allen pushed to keep them apart. She asked for Light Up to be its own line item and said food trucks could still come to Light Up so residents get the same experience as in past years, even if the regular series ended. "I'd like to make sure we protect Light Up Windermere, whether it's a food truck or whatever," she said.
The town's events calendar now lists Food Truck Night as "Canceled Until Further Notice." The Windermere Neighbors page still calls Nov. 20 "Light Up Windermere & Food Truck Night." Food trucks may well line up on Nov. 20 as part of Light Up, while the standalone monthly series stays off the calendar. The town's own announcement says only "food."
Pausing the series has a cost beyond missing dinner on the square. The Historic Preservation Board gets some of its funding from Food Truck Night proceeds. Haines raised that at the hearing, arguing that cuts were landing on the town's volunteer boards instead of being spread across the budget. Haines and Stroup both said residents have been asking for Food Truck Nights. Haines said several parents of school-age children told her they don't need a DJ or band and simply want to gather. One resident suggested bringing an approved playlist to play on a speaker.
Stroup asked for a future council discussion about bringing the series back. The mayor set the condition. Council would need "hard numbers" on cost and staff time first, because "the bottom line is, we still have to cut something else to bring it back." Smith called the budget a "living and breathing document" that council can adjust later. If Food Truck Night comes back, it will come through a council agenda item, which makes town council meetings the place to watch.
The Rest of the Season Runs on Volunteers
With the town funding one evening, most of the remaining November calendar around Town Hall is organized by someone other than the town. Here is what's coming up, in order:
- Monday, Nov. 9, and Monday, Nov. 23: Game Night at Town Hall. The town hosts these on the second and fourth Mondays of each month. Bring a favorite game and snacks. Groups and people coming alone are both welcome, and the town asks attendees to RSVP through its TeamReach group with the code TOWGAMENIGHT2026. On the same second-and-fourth schedule, December's dates are Dec. 14 and Dec. 28.
- Wednesday, Nov. 11, 10 a.m.: Veterans Day Observance. The Rotary Club of Windermere hosts the annual ceremony at Town Hall.
- Nov. 11, after the ceremony: Smiles for Seniors. The Windermere Legacy Fund and the Rotary Club need volunteers to pack gift bags with essentials and holiday treats. Meals on Wheels will deliver the bags to seniors before the holidays. Sign-up details are on the town's feed, or email [email protected].
- Friday, Nov. 20: Light Up Windermere at Town Square Park.
Looking further ahead, the West Orange Foundation hosts Windermere Wine & Dine on Saturday, Feb. 6, 2027, bringing together restaurants and wineries to raise money for community programs. Tickets went on sale Oct. 24.
The common thread is who's behind each one: Rotary, the Legacy Fund, a foundation, a church, a dance academy, and neighbors carrying board games into Town Hall on a Monday night. The town provides the room, the park and a smaller set of lights.
A New Reason to Stay on Main Street After the Lights Come On
Downtown is also getting a small addition owned by people who live here. The Observer reported in early October that Penelope's Coffee had nearly finished renovations at 507 Main St., on the same street as Town Square Park, with no opening date announced yet. Owners Leti Freitas and Joe Harris are Windermere residents. They plan to serve Orlando's own Lineage Coffee along with baked goods. On Instagram, they said they hope Penelope's becomes a place to "unwind, take a quick lunch break or catch up with an old friend." It's expected to open this fall. If the doors are open by Nov. 20, a coffee before the 7 p.m. lighting would be an easy addition to the evening.
For a Keenes Pointe household planning the holidays, the practical result is simple. Nov. 20 is the one night on the town's tab. The lights will likely be concentrated around Town Square. Whether food trucks join will be clear once the town posts final details. The rest of November is open to anyone willing to show up for a ceremony, a volunteer shift or a game.
Hosting family over the holidays and wondering which Windermere nights are worth bringing them to? Kara keeps up with the Main Street calendar as closely as the market, and she's always happy to talk through either. Kara Wisely is a quick message away. Let's Connect.
