Delavan’s first “Main” Street Cruise-In rumbled to life in September 1989, the kind of small-town experiment that quickly proved it had staying power. The idea came from Jerry Engel, who saw an opportunity after the “Show and Shine Car Show” drew an enthusiastic crowd at that year’s Fall Festival. With momentum on their side, Greg Dirks and Denzil and Carol Cain—who had chaired the Show and Shine—set to work planning a dedicated Cruise-In event downtown.

That first September gathering was such a hit that the trio didn’t hesitate to keep it going. They chose the third Saturday of each month, secured permission from the city to block off the 300 block of “Main” (Locust) Street, and launched the first full season Cruise-In the following April. Between 30 and 40 vehicles filled the block that spring evening, with Greg  Dirks and Denzil Cain guiding drivers into place while Carol Cain spun a soundtrack of ’50s and ’60s classics that instantly set the mood.

Winnie’s Restaurant—owned by Jerry and Lin Engel—stepped in as the original sponsor, donating door prizes and helping build the Cruise-In’s reputation as a relaxed, family-friendly night out. Spectators wandered among the antique and classic cars, swapping stories and admiring chrome. Boy Scout Troop 61 sold hot popcorn. The formula was simple, but it worked: good music, good company and a shared love of cars.

As the years rolled on, the Cruise-Ins became a signature part of Delavan’s summer rhythm. After Winnie’s closed, the Delavan Optimist Club took over sponsorship, with area businesses continuing the tradition of donating door prizes. The events grew livelier, adding 50/50 raffles, games for cruisers and spectators, Loud Muffler competitions and even flame-throwing exhibitions. Some nights drew more than 100 vehicles, lining Locust Street with everything from lovingly restored classics to eye-catching custom builds.

Twice, the Cruise-In community paused to honor individuals whose dedication had shaped the event. One tribute recognized Pete Connell, who restored three 1964 Ford Galaxies and never missed a Cruise-In from the very first gathering until his passing on July 22, 1991. Another honored Ron Holmes, a member of Delavan’s E.S.D.A., who faithfully handled traffic control at every Cruise-In until his death on August 29, 1992. Their contributions—and the memories they left behind—remain woven into the event’s legacy.

More than three decades later, the Cruise-In is still going strong. The Optimist Club continues its sponsorship, and leadership has passed to a new pair of steady hands: longtime organizer Greg Dirks and Steve Skinner, who now help guide each season’s events. The music, the cars, the conversations, and the sense of community remain much the same as they were in 1989.

What began as a simple idea—close the street, invite the cars, play some oldies, and see who shows up—has become one of Delavan’s most enduring traditions. The “Main” Street Cruise-In isn’t just a summer event; it’s a piece of hometown history that keeps rolling forward, one third Saturday at a time.
This first Cruise-In of 2026 is Saturday, April 18, from 4-8 p.m.