For one evening each October, the ballfields and pickleball courts at Wimberly Field give way to something considerably less athletic. Decorated car trunks pop open, candy comes out by the cooler-full, and the park at 4000 NE 3rd Avenue becomes what the City of Oakland Park calls a Halloween playground. The city's annual Halloween Bash is set for Friday, October 30, 2026, and admission is free.
The city bills it as "A Not-So-Scary Night of Family Fun," a phrase that does a fair amount of work. This is not a haunted house with fog machines and jump scares. It is the other kind of Halloween, the one built for the stroller set and the grandparents trailing behind them: decorated vehicles, candy, costumes, inflatables, music, games and seasonal attractions, all arranged so that a family can move through the evening without anyone dissolving into tears.
The centerpiece is the Trunk or Treat, which the city describes as its signature activity. For the uninitiated, trunk-or-treating is a parking-lot inversion of the front-porch ritual: instead of walking a neighborhood block and knocking on doors, kids circulate among cars whose owners have decorated their open trunks and hatchbacks as miniature scenes and hand out candy from the back. It has become a staple of church lots and school parking lots across the country over the past couple of decades, partly as a way to compress trick-or-treating into a contained, well-lit space, and partly because a lot of people genuinely enjoy turning a Honda into a spider's lair.
Around the cars, the evening adds the rest of the fairground furniture. There are costume contests, which the city has promoted in past years alongside dance competitions hosted by a DJ. There are inflatables to bounce around in, an abundance of Halloween candy, and the Hay Find, a seasonal attraction the city lists among the event's draws. Music runs through the night, and the whole thing is laid out as a place for families to celebrate together rather than a show to sit and watch.
That the Bash happens at Wimberly Field is itself part of the appeal. The address is a large athletic complex rather than a single ballfield, with baseball and softball diamonds, soccer and football fields, lighted basketball courts, pickleball courts, a concession stand, restrooms and a shaded playground. In other words, it already has the parking, the open lawn and the infrastructure that a community festival needs. On Halloween, the diamonds and courts simply become real estate for bouncy houses and candy lines.
The event has settled into the city's calendar as a recurring tradition rather than a one-off. In 2025 the Bash ran on Friday, October 24, from 6 to 9 p.m. at the same address, with the same free admission and much the same lineup of costume contests, DJ-led dancing, inflatables and candy. Local family-event roundups have taken to listing it as a community favorite, and neighborhood groups around the city promote it alongside the rest of the municipal calendar. The 2026 edition shifts to the Friday before Halloween itself, October 30.
That scheduling is worth noting for anyone planning around it. Past editions have stretched three hours; this one is posted as a single evening event, so families who want to work the trunk-or-treat line and still make the costume contest should arrive at the start rather than drifting in late. The city's calendar lists no ticket, no registration and no capacity limit, which is the point of a municipal park event: you can decide at 5:45 that the kids are going as a dinosaur and a slice of pizza, and still go.
The Bash also sits inside a broader Halloween week in Oakland Park. The city has scheduled a Halloween Storytime at City Hall on Tuesday, October 27, 2026, at 10 a.m., inviting kids five and under to come in costume for a morning of stories. Between the two, a family can fill a week with the holiday without ever leaving city limits.
There is a certain logic to a city like this throwing a not-so-scary party. Oakland Park's history is a story of reinvention. The first permanent non-native settlers, Tom and Netta Whidby, arrived from Georgia in 1901, when the area was known as Colahatchee and given over to bean and pepper fields. In 1923 a Miami development company announced that Colahatchee would henceforth be the subdivision of Oakland Park and threw a barbecue to sell the idea; more than 5,000 people from Dade, Broward and Palm Beach counties showed up for the free food. The town incorporated as Floranada in November 1925, then reincorporated as the City of Oakland Park on July 1, 1929, after residents voted down offers from Fort Lauderdale and Pompano Beach to absorb them.
A hundred years on, the city's biggest communal gatherings still run on the same formula that packed them in during the boom years: free admission, open gates, and enough going on that the neighbors turn out. The Halloween Bash is a smaller-scale version of that impulse, but the shape is recognizable. You show up, you see people you know, and the kids come home with more candy than is strictly advisable.
Wimberly Field is at 4000 NE 3rd Avenue in Oakland Park, 33334. The Halloween Bash runs Friday, October 30, 2026. Admission is free.