Remembering Winterfest: The Cold-Weather Cousin to the Big Gig

Jul. 10, 2017
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An ad for the 1989-90 edition of Winterfest

For over a decade, Summerfest had a snowy counterpart festival know as “Winterfest,” a longer, but lower-profile event that was meant to attract visitors to Milwaukee during the tough-draw wintertime months. While Winterfest was never able to become as ingrained a part of the local season as Summerfest, it did have some memorable moments. With the Big Gig’s 50th edition now past, let’s revisit Milwaukee’s long-lost “Big Cool.”

Mayor Henry Maier, the driving force behind the creation of Summerfest, had proposed a cold-weather festival for the city as far back as 1969 – Summerfest’s second season. The proposal floundered until 1978, when the very first Winterfest was held at various sites around the city, with the primary action taking place at the downtown MECCA. The festival ran ten days and featured such varied entertainment as a winter sports exhibition, an outdoor film festival (meaning films that featured the outdoors, shown indoors), an ice sculpting competition, and a checkers tournament. The event was repeated in 1979, renamed “Winter Festival,” but a dip in attendance caused the event to the shelved.

Maier brought the idea back in the mid-1980s, hoping to set it up as an official wintertime version of Summerfest. But nothing came of the proposal until 1988, when the city announced “Icebreaker: America’s Winter Festival.”  With the intent of creating a nationally-recognized winter festival, organizers secured comedian Richard Belzer and the new wave band Duran Duran to headline the four-day event. Icebreaker was also given a pair of mascots: a Jack Frost-esque character named Isa, who lived beneath the frozen waters of Lake Michigan, and a sunglasses-wearing pooch named Sundog who, as the Icebreaker mythology went, was discovered by Isa in a magical, ice-encrusted egg.

Despite the big name acts and the magical powers of Isa and Sundog, Icebreaker was a one-time deal. The event was put under the control of Milwaukee World Festival, Inc., the parent organization of Summerfest, in the summer of 1989, and returned to its roots with a rebrand featuring the familiar Summerfest smile (with a winter cap) and a name change back to Winterfest. The various events of the fest were stretched out to cover six full weeks in late 1989 and early ’90, with the primary attraction being a public ice skating rink in Cathedral Square Park. The festival was an instant success and drew headliners like Michael Bolton, the Georgia Satellites and Kenny Rogers over the next several years. Winterfest’s offerings including professional figure skating, pro wrestling and Native American dance exhibitions.

Another staple of Winterfest in the early 1990s was stand-up comedy. And one up-and-coming comic was responsible for the most controversial chapter in the fest’s short history. Then-SNL cast member Chris Rock was booked into the “Comedy Cabaret,” located in an auditorium at the former high school adjacent to St. John’s Church in downtown. Given the venue, organizers had posted a notice on the green room door asking performers not to use profanity in their acts. As Rock took the stage, he told the audience about the notice and exclaimed, “Now I don’t know what the fuck to say!” Rock did his usually routine, which was so blue that Summerfest executive director Bo Black, who was in the crowd that night, nearly stopped the show. From that point forward, comedians were no longer permitted to perform on church grounds.

Into the late 1990s, Winterfest focused on local acts for their entertainment stages. Familiar names like Willy Porter, the Gufs, the BoDeans, and Citizen King became regular Winterfest performers. The most anticipated part of the fest remained the ice-skating and, when the county announced plans to build a permanent rink (in Red Arrow Park), the Milwaukee World Festival Board voted to discontinue the festival after its 1997-98 edition.

The festival, in name only, was reborn in 2011 when “Milwaukee Winter Fest” was held at the Wisconsin Center. The new fest was collection of rides and family-focused events. Currently, the Urban Ecology Center holds an annual Winterfest, a single-day event that is centered on crafts, sledding, and hot cocoa.  


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