The winner of the Route 66 Driving & Photo Contest, with more than 20 photo entries, is Jeannine Jeskewitz. Linda Barnes is the second place winner of the contest, also with more than 20 photo entries. Both women are members of the ‘Stilettos on Steel,’ a national female motorcycle riding group.
The group holds an annual Midwest Meet-Up where all chapter members of the Midwest region and beyond can gather to celebrate ‘sisterhood.’ In July of 2026, the Illinois chapters will be hosting this event for the first time. “We decided to plan this along Route 66 between Chicago and Springfield, Illinois,” says Jeanine Jeskewitz. “We needed to schedule a weekend trip this summer for research! So, in August this year, five of us rode from Chicago to Springfield, to investigate the sites along the route.”
Route 66 photo contest winner’s photo collage, August 2025 – photos by Jeannine Jeskewitz
“My friend Linda, who is also our Illinois State Coordinator, found the Overlook Maps Rt. 66 contest and app and asked me if I would download the app. As we rode along Route 66, we used the Overlook app to track the important historical and fun sites along the way. It was super easy to use, to locate the stops and load our photos at each location. Our trip was AMAZING. I’m a huge fan of Route 66,” continues Jeannine. “The app made our trip much more fun and so easy because we didn’t need to research each stop. The app did it for us, so we could spend more time exploring!”
Route 66 photo 2nd place winner’s photo collage, August 2025 – photos by Linda Barnes
Presented by Overlook Maps, American Road Magazine and the National Scenic Byway Foundation.
Thanks to the NSBA Visit Springfield Illinois Sponsor!
