For many residents, the award-winning parade is the highlight, but organizers say the event is now a full-day celebration that starts well before the first float rolls down the street at 7 p.m. Streets begin closing at 1 p.m. so crews can rope off viewing areas and prepare the route. By mid-afternoon, floats start arriving, lining up between 3 and 5 p.m. and bringing with them the familiar excitement that builds as dusk approaches.

Food trucks are part of the experience again this year, setting up in front of the courthouse and MidwestOne Bank by 4 p.m. Local businesses are also opening their doors earlier in the day to welcome families looking to shop, grab a meal, or enjoy the downtown atmosphere. “We have lots of businesses that will be open and ready to greet you,” says Angella Foster, Oskaloosa Main Street Director.

Inside Penn Central Mall, children’s activities will be offered throughout the day, making it easy for younger families to take part. Shuttle services will also be available from area churches, giving visitors a convenient option to park away from the busy downtown area and ride in.

While parade preparations unfold behind the scenes, holiday events begin early. “Businesses are going to be opening anywhere from eight to 10 in the morning,” says Foster. One of the day’s highlights includes an 11 a.m. performance of The Best Christmas Project Ever at the George Daily Community Auditorium. Many families plan their entire day around it. “You can come to the production, have lunch, do a little shopping, and then go have dinner,” she said. From there, families can head straight to the parade route.

Music also plays a role in the evening lineup. Members of the Oskaloosa City Band will perform around 6 p.m., offering a half hour of holiday music before some musicians join their own parade floats. Their performance has become a familiar and favorite tradition.

This year’s parade theme, “Holiday Joys and Toys,” invites float designers to bring playful, creative, and nostalgic ideas to life. Organizers expect that creativity to shine, especially with a record number of participants. “We have 18 new entries that we’ve never had before. I think we’re close to 75 entries,” says Foster. “That’s the largest number since I have been here for.” All floats will include lights, a detail she emphasized after hearing past requests from parade-goers.

Oskaloosa Main Street also addressed one of last year’s concerns: dim lighting along Third Avenue. Working with Musco Sports Lighting, the parade route will include five additional light units to brighten areas that were previously difficult to see. “It will light the area better there this year,” Foster said.

The event’s history is part of what makes it so meaningful. National travel site Iowa Road Trip has called it the largest and longest-running lighted Christmas parade in Iowa, a point of pride for Oskaloosa. “This is our 38th annual Lighted Christmas Parade,” Foster said. “Oskaloosa Main Street will celebrate 40 years next year, so this parade is almost as long-standing as Main Street itself.”

The continuity is visible in the crowd each year. Families who once bundled up their young children for the parade now return with children of their own. “The kids that started off coming to see that parade, when it started, are now bringing their kids,” she said. “It’s fun to see the families that are all here.”

Over time, organizers say the sense of community around the parade has only deepened. There may be more floats and more lights today, but the heart of the event remains simple. “You don’t need all the bells and whistles,” she said. “It’s different organizations being a part of it. You may just be walking through it, and you get to see your neighbor. It’s one of those homey, great times that is just magical.”

For many, the parade is less about candy or giveaways and more about the shared experience of gathering downtown on a winter night, seeing familiar faces, and taking in the glow of lights reflecting off historic buildings. Some residents return home for the holidays, making the parade a place to reconnect. “You get to see your classmate you haven’t seen for 10 years,” she said. “Or you get to bring your grandkids. It’s more for the lights and the experience.”

With a record number of floats, a full schedule of activities, and a theme that invites imagination, organizers anticipate one of the most memorable celebrations yet. “I think we covered it all,” she said with a smile. “You just need to come and see it.”