Siblings Paul and Annamarie Weaver steer their carnival cab, 1964. (Photo courtesy of the Weaver family)

Originally appeared in the Fall 2021 Gazette, by Helen Weaver.

Phoebe Massey Ryerson was looking to raise funds for the new Winnetka Community Nursery School back in 1945 so she decided to host a “fair” in her backyard. The success of that event began a tradition that families have enjoyed for decades. The Winnetka Children’s Fair will celebrate its 75th anniversary in June 2022. The fair, organized by the nursery school’s board, has been held every year except for this year and last when it was cancelled due to the coronavirus pandemic.

The first few fairs were held at private homes, but since 1948 the fair has been held at Winnetka’s Village Green. While rides and games have been a part of the fair since its beginning, the specifics have changed over the years. In the early years, children seemed satisfied by simpler pleasures. A 1946 Chicago Tribune review claimed that “one of the favorite attractions… was the ‘Spring Jump,’ which consisted of jumping from a tree stump to a blanket covered mattress on the ground.” In 1949, one of the games was “throwing wet sponges at a human target.” The 1950’s fair featured hoof-print autographs from Misty of Chincoteague, the horse hero of the book by Marguerite Henry.

One of the most beloved features of the fair was the “Main Show,” which got its start in 1951 as “A Beautiful Land,” a musical pageant depicting events in Winnetka history from 1670 to 1900. That same year the fair was extended to a two-day event. The main show started as live performances of original productions written and directed by community volunteers, showcasing dozens of children and sometimes a famous adult or two. Studs Terkel narrated the 1955 performance of “Robin Hood” and teenage television star Susan Heinkel appeared in 1958’s production of “The Little Tailor.”

By 1959, the audio was pre-recorded, sometimes by the actual casts and sometimes by other actors, making rehearsal less strenuous and sound quality better. Cast sizes grew as roles were given to two sets of performers, sometimes including hundreds of children. In 1981, the Chicago Tribune’s Howard Reich wrote: “the big draw at each year’s edition of the fair is the musical show, a Broadway-style extravaganza performed entirely by local school kids. This year’s feature is an updated version of ‘Alice in Wonderland,’ and it spotlights more than 270 children.”

The Weaver family has a long Children’s Fair of Winnetka history of involvement with the Winnetka Children’s Fair. Paul Weaver and his sister Annamarie attended annually beginning in toddlerhood in the early 1960s. Paul appeared in at least two main show events including “You’re A Good Man Charlie Brown” in the early 1970s. Brian, Eliza, and Joanie Weaver all performed in multiple main shows during the early 2000s. Eliza remembers: “I was in the main show for five or six straight years. I have great memories of being a kite in ‘Mary Poppins’ and a munchkin in the ‘Wizard of Oz.’”

George Massey Jr., the brother of fair founder Mrs. Ryerson, directed many of the shows during the 1960s. Other longtime volunteer directors/producers include Mr. and Mrs. Robert C. Woolson, Gail Johannson and Jeff Kane.
Unfortunately, the main show era ended in 2009 as fair volunteers got harder and harder to recruit.

The original goal of the fair was to raise money to support the nursery school, but as the scope of the fair has changed over the years, so has its primary objective. The Chicago Tribune’s Gregory Trotter wrote in a 2013 interview of fair
Chairperson Elizabeth Smylie: “Though the fair raises money for the nursery school, it’s not really about the money. The intent of the fair is actually to be a gift to the community.”