
The Winnetka Children’s Fair, back after a two-year hiatus, features slides, rides, and fun for the whole family.
Put those tech gadgets down, kiddos. The Winnetka Children’s Fair is a return to old school fun, and it’s back after a couple of years off. The fair is celebrating its 75th Anniversary with bouncy castles, rides (zip line, Giant Fun Slide, bungee jump), hot dogs, fancy snow cones, and the beloved Candy Castle.
For parents, there will be beer and wine from Winnetka’s own Good Grapes, as well as a retrospective display created by the Winnetka Historical Society with photos and memorabilia from the fair over the decades.
The fair was started in 1945 initially as a fundraiser for Winnetka Community Nursery School. It was originally held in a local resident’s back yard but moved to the Village Green in 1948. The Board of Directors of Winnetka Community Nursery School sponsors the fair.
“It’s been held in the Village Green every year since 1948 except for the two years that we had to take off for COVID,” says Catherine Ernst, co-chair of this year’s fair. “It’s grown to become a very large community-wide event, but I think most people don’t even realize that it’s put on by the preschool and not the village.”
More than 4,000 people from across the North Shore attend the fair each year, and it’s all run by parents at the pre-school. Over 200 volunteers also pitch in to keep it running. Corporate sponsors for this year’s fair include @properties, BLG Capital Advisers, BMO Wealth Management, DVTrading, Go Green Winnetka, LP Group, Inc., North Shore Community Bank, Ruffolo Landscaping, and Shore Community Partners.

The 75th Winnetka Children’s Fair will take place on June 9 and 10. With the exception of
2020 and 2021, the fair has been held at the Village Green every year since 1948.
“It’s the starting kickoff for the summer. The kids get out of school, and they race to the Village Green on their last day,” says Ernst. “We have pony and camel rides and games. We’re going to have a Kona shaved ice truck this year which is kind of a fancier snow cone.”
Perhaps most importantly, the Candy Castle will be back. At the fair since the ‘80s, the Candy Castle is a wooden structure that kids can enter and fill their bags up with the candy of their choice.
“I know that for some people who grew up in Winnetka, the Candy Castle is a very beloved attraction for them,” Ernst says. “It’s something that they always remember and associate with the children’s fair.”
Because of the fair’s long history of providing family fun, it holds a special place in many North Shore resident’s lives. Not many community traditions date back to the Truman administration.
While the fair has changed over the years, it has stayed focused on providing old school fun for kids of all ages, according to a 2021 article in the Gazette, the newsletter of the Winnetka Historical Society,
“In 1949, one of the games was ‘throwing wet sponges at a human target’,” the article states. “The 1950s fair featured hoof-print autographs from Misty of Chincoteague, the horse hero of the book by Marguerite Henry.”
“I think it’s a really big part of the tradition of growing up in Winnetka and the surrounding areas. It’s definitely been a great way to bring the community together, especially with being off for two years.” Ernst says. “I think it’s going to be especially meaningful to be bring it back this year. Celebrating this huge milestone is what people are really looking for these days and it’s going to be such a special way to kick off the summer.”
For Ernst, her involvement in planning the fair this year is personal. Her daughter attended Community Nursery School and her brother, Jeff Warren, attended nearly 30 years ago. Her mother, Mary Warren, was involved in planning the fair back while her brother was there.
“My daughter started out at Community Nursery School, and I just fell in love with the community and everything that the preschool stands for. My son is currently in the program there,” Ernst says. “I joined the board at the beginning of COVID and it’s a way of being involved in the community and also being a part of something that impacts my children’s lives.”
The Winnetka Children’s Fair takes place on Thursday, June 9, from 12:30 to 8 p.m. and Friday, June 10, from 10 a.m. to 2 p.m. at the Village Green, 525 Maple Street in Winnetka. Admission is free; tickets for rides, activities, and food and drink will be available for purchase. For more information, visit winnetkacommunitynurseryschool.org.