"I think we can cut smaller item projects in order to keep our town events for our residents," Council Member Tom Stroup said in September. He was arguing to put Light Up Windermere back into a budget that had already dropped it. Orange Observer reported his comments from the town's first budget hearing on Sept. 3.
He won that argument, and Light Up returns on Friday, Nov. 20. Still, the November that reaches Town Square this year is a different arrangement than past years. The town is paying for less of it. A local church, a dance academy, an arts group, and possibly some residents are covering more of it.
What the budget debate cut, and what it put back
The cuts started at a budget workshop on Tuesday, July 28. Town staff proposed eliminating or suspending two town-sponsored events, Light Up Windermere and Food Truck Nights. The reason was to prepare for spending cuts if Amendment 3 passes in November. According to the Florida Division of Elections summary, the measure would raise the homestead exemption for non-school property taxes to $150,000 in 2027 and $250,000 in 2028. It would also adjust that exemption for inflation, lower the assessment cap on non-homestead property from 10% to 5%, and limit what local property taxes can be used for. The vote is Tuesday, Nov. 3. Whatever the result, Windermere has already planned its holiday season around the possibility.
Here is how each piece came out:
- Light Up Windermere: Restored. Town Manager Robert Smith told council that hosting it can be absorbed into the current budget.
- The holiday lights: Reduced. The town spent $35,955.27 last year on its contract with Humbug Holiday Lights, which covered delivery, installation, removal, and maintenance. On Sept. 8, council voted 4-1 to let staff spend up to $25,000 on lights this year. Humbug's quote for a reduced scope covering the area around Town Square came in at $24,997. A second company quoted $49,000 and was working on a quote for a reduced scope.
- Food Truck Nights: Still suspended. The town's Food Truck Nights page says "suspended until further notice," and the Halloween Food Truck Night set for Oct. 23 was canceled.
The cap of up to $25,000 is roughly a third less than what the lights cost last year. Expect the glow to stay closer to Town Hall and Town Square Park than it did in 2025. Mayor Andy Williams said he had been talking with residents willing to help pay for holiday festivities.
The food truck suspension reaches further than one Friday night. Council Member Brandi Haines pointed out that the cuts fell on events that help fund the Historic Preservation Board and the Windermere Tree Board, and that Historic Preservation gets part of its money from Food Truck Nights proceeds.
Who is running November on Town Square
With town spending reduced, the calendar holds together because other groups are running much of it. Smith explained to council that Family Church of Windermere usually provides the activities in front of Town Hall at Light Up, and White Swan Academy performs indoors and outdoors, all at no cost to the town. The biggest weekend event of the month is organized by Windermere Arts, not the town. Here is the month in order:
- Fridays, Nov. 6, 13 and 20, 9 a.m. to 1:30 p.m. The town's Farmers Market sets up at Town Square Park, 520 Main St. This weekly event survived the cuts. The town calendar also lists it for Dec. 4 and 11.
- Wednesday, Nov. 11, 10 to 11 a.m. The Veterans Day Celebration takes place at Town Hall. Right after, from 11 a.m. to noon, volunteers pack bags for Smiles for Seniors at 520 Main St.
- Saturday and Sunday, Nov. 14 and 15, 10 a.m. to 5 p.m. Windermere Arts hosts its second annual Holiday Extravaganza around Town Square on Main Street. The organizer's materials describe fine art from artists, including paintings, sculpture, photography, quality jewelry, and gifts. Booths go on the Town Hall Square grounds and along Main Street. The materials also list music, face painting, pictures with Santa, a talent show, and food and drinks for purchase.
- Friday, Nov. 20. The market runs in the morning and Light Up Windermere takes over in the evening. Details below.
The Holiday Extravaganza is the weekend when most Christmas shopping can happen within walking distance of Town Hall. It also falls in the town's tighter budget year without drawing on that budget.
Nov. 20 is the longest day on Town Square
The town's Oct. 12 announcement promises "an evening of food, live performances, and holiday festivities" and says more details are coming. It hasn't posted start times or a lineup yet. For now, last year's event is the best preview, and it should be read as a 2025 example, not a 2026 schedule.
Orange Observer's 2025 preview listed a 5:30 to 9:30 p.m. event at 520 Main St. Guests were invited to bring chairs and blankets. The program included food trucks, a DJ truck, a Bubble Bus, and the holiday lighting. The paper's photo gallery from that night showed Family Church choirs, ballerinas from White Swan Academy, and a countdown to the lighting at about 7:15 p.m.
Two things may look different this year. First, the lights. If the reduced Town Square scope is what gets installed, the countdown will light up a smaller area than last year's. Second, the food. Light Up used to share the night with Food Truck Nights. During the budget hearings, Council Member CT Allen suggested the town could keep the regular Food Truck Nights suspended and still bring trucks to Light Up so it feels like past years. "I want Light Up Windermere to be a separate line item," she said, as Orange Observer reported. The town's announcement mentions food but doesn't say food trucks. Check the town's site the week of the event before you count on dinner from a truck.
If you're planning the whole day, the Friday market wraps up at 1:30 p.m. That leaves the afternoon before Light Up, and Main Street has a few new options for filling it.
Filling the gaps on Main Street
The Main Street businesses within walking distance of Town Square matter more in a year with fewer town-run nights out. Two are new or about to be.
Fresco Pizzeria, 527 Main St. The restaurant's own Windermere page now says "Now Open." The menu covers wood-fired pizza, handmade pasta, sandwiches, baked goods, and Italian desserts. It's a few doors from Town Hall, so it works for a sit-down meal before the Nov. 20 lighting or a lunch break during the Extravaganza.
Penelope's Coffee, 507 Main St. Orange Observer reported Oct. 2 that renovations were nearly finished and the café expected to open this fall, though no exact date had been announced. If it opens before the market Fridays, it will add a coffee stop at the other end of the same block.
Two established spots are close by. Dixie Cream Café at 434 Main St. serves breakfast and lunch, a good fit before or after a morning at the market. Tim's Wine Market at 428 Main St. is a short walk from the Holiday Extravaganza if your holiday shopping list includes a bottle. Hours change around the holidays, so check before you go.
For getting there, the town opened portions of the Ward Trail and its new pedestrian bridge in August, according to Orange Observer. The project covers about a half mile of shared-use trail with drainage improvements and landscaping, and the bridge is open to pedestrians, cyclists, and golf carts. Crews were scheduled to keep working through the fall on the final path sections and landscaping, so some stretches may still be unfinished when you go. Mayor Williams described it as "a safer connection between our neighborhoods, parks" and more. On a Friday when parking near 520 Main St. fills up twice, once for the market and again for Light Up, a golf cart or bike route into downtown is worth knowing about.
Council adopted the town's 2026-27 budget unanimously on Sept. 16: $12,464,394.17 in total, with an operating millage of 3.7425. Light Up survived in that budget because council members pushed for it. Whether it looks the way it used to depends on Family Church, White Swan Academy, Windermere Arts, and whichever residents help with the lights.
I live just up the road in Historic Downtown Winter Garden, and I care about these small-town traditions as much as anyone. If you have questions about Windermere's downtown, or want to talk over what's changing in the area, Kyle Gunter is glad to hear from you. Let's Connect.
