Winfield hosted its 55th annual Good Old Days Festival over the weekend of Sept. 5-7. The event featured live music, food vendors, kid zones, trolley tours, and a parade in downtown Winfield, near the intersections of Church Street and Beecher Street.

This year’s theme was honoring Winfield’s legends. Harold, a World War II veteran and former principal at Winfield School, served as one of the parade’s grand marshals on Sunday.

The festival, which dates back to 1968, is organized by community groups including the Knights of Columbus, the Winfield Lions Club, and the Winfield Historical Society. A ribbon-cutting ceremony also marked the opening of a new fire station in Winfield.

Festival organizers anticipated large crowds, so six commuter parking lots were designated for visitors. Additional parking was available at Northwestern Medicine, located on the north side of Winfield Road. By spreading out options, the town hoped to reduce traffic congestion and make it easier for families and out-of-town guests to access downtown.

Local favorite Rob Russo and the Loose Screws performed a three-hour set on Sunday afternoon, bringing a mix of rock and blues to the main stage. The free concert was one of the last events of the weekend and drew a large crowd of festivalgoers who gathered on the lawn with lawn chairs and picnic blankets. Many attendees stayed through the final song, which served as a closing note to the community celebration.

The Kid Zone offered classic carnival-style games, with Plinko among the most popular for younger children. Families also participated in a “passport” coloring contest, encouraging kids to visit multiple activity stations. The traditional prince and princess crowning ceremony gave children the chance to take the stage and be recognized, a highlight for many parents and grandparents in the audience.

Food options stretched across downtown Winfield, ranging from festival staples like funnel cakes and lemonade to local specialties. One highlight was the meatball eating contest sponsored by Caliendo’s on Saturday afternoon, which brought out enthusiastic competitors and a cheering audience. Vendors reported steady business throughout the weekend, with many families stopping for meals in between rides, games, and performances.

Alongside games and inflatables, the Kid Zone also featured a petting zoo where children could interact with goats, rabbits, and other small animals. Parents gathered nearby as children fed the animals and posed for photos. These family-oriented activities gave younger visitors a chance to engage with the festival at their own pace while older siblings enjoyed rides or competitions elsewhere downtown.

From Friday evening through Sunday, food vendors were a steady presence on the main streets. Local restaurants joined outside vendors to serve everything from barbecue to Italian ice. For many, the food was a central part of the festival experience, offering a chance to sample both longtime favorites and new specialties.

Competitions were scheduled throughout the weekend, giving both children and adults the chance to participate. Events ranged from lighthearted shoe-toss games to the more unusual glow-in-the-dark axe throwing, which quickly became a crowd favorite. These contests reflected the festival’s emphasis on variety, offering activities for all ages and skill levels.

The festival was heavily volunteer-driven, with local families helping to run booths, organize parades, and staff children’s activities. Their participation reinforced the sense of community that has defined Good Old Days for more than five decades. For long-term residents, the festival is both a tradition and an opportunity to reconnect with neighbors.

Booths lined the downtown streets, allowing small businesses, nonprofit groups, and local organizations to share information and sell products. From handmade crafts to home services, the variety of vendors highlighted the role of Good Old Days as not just a festival but also a showcase for Winfield’s business community.

Sunday afternoon’s parade, which ran from 1–2 p.m., featured community floats, local marching bands, and civic groups. Families lined the streets to watch the procession, with children gathering candy tossed from participants. The parade has been one of the central traditions of Good Old Days since its inception in 1968.

Beyond the games and performances, many attendees took time to enjoy the setting of the festival itself. Downtown Winfield’s riverfront gazebo and landscaped flower beds offered a scenic backdrop for photos and a quiet place to step away from the bustle. For some visitors, these natural spaces are as much a part of the tradition as the parade or food vendors.