Pekin, Illinois may not sit directly on Route 66, but it’s home to one of the highway’s biggest champions—Jessica Anderson. In 2024, Anderson became the first woman from her hometown and her state to win a national Route 66 beauty title. She not only claimed Miss Illinois Route 66, but also the highest honor, Miss National Route 66 Supreme, awarded to the contestant with the top overall score across all divisions.

What makes Anderson’s win remarkable is her journey to get there. Days after turning 40, she entered her first-ever in-person beauty pageant, held in Barstow, California. Just a few years earlier, she had undergone bariatric surgery, losing 100 pounds and gaining the confidence to take a chance on something new. On a modest substitute teacher’s salary, she relied on second-hand gowns, borrowed outfits, and a vintage waitress uniform from the 1950s provided by Tootsie’s Fashion in Benton, Illinois. Owner Karen Semanski, a Route 66 enthusiast and vintage fashion expert, helped sponsor Anderson and supported her cross-country dream.

Despite limited funds—she even stayed in hostels and relied on buses—Anderson made her way west, braving Los Angeles traffic and even accepting a ride from a good Samaritan who noticed her sitting and waiting when her Lyft never showed up. She capped off the trip by visiting the Santa Monica Pier and the iconic “End of the Trail” sign, fulfilling a lifelong dream.

A Life Shaped by the Mother Road
Anderson’s love for Route 66 began in childhood. Her mother took her to iconic attractions such as Meramec Caverns and the Illinois State Fair, while both of her parents worked in Route 66 towns. Later, as a college student at Illinois State, the sight of the brown highway signs always made her smile.

This summer, she attended numerous Route 66 events, from the Great Race stop in Springfield, Illinois, to the neon lighting ceremony in St. Robert, Missouri, where she addressed the crowd. She also appeared at the opening of the new Route 66 Park in Carpenter’s Park, Springfield. At many of these gatherings, she delighted children by handing out Hot Wheels cars she bought herself. She even made time to visit servicemen and women at Fort Leonard Wood.

Locally, Anderson has always embraced car culture. She fondly recalls cruising Pekin’s streets with the late Ronald Wilson of Wilson Towing, known for his car collection and community support. She rode in his 1964 Ford Galaxie during the Pekin Marigold Parade and worked alongside him at races in Spoon River and Lincoln Speedway. His recent passing was a personal loss: “Ron always believed in me and my dreams,” she shared.

Pageants With Purpose
Though new to traditional pageants, Anderson is no stranger to the stage. For eight years, she has competed in vintage pin-up contests, where women showcase classic fashion and personalities reminiscent of Lucille Ball. Her charisma and creativity have earned her crowns across the Midwest and beyond.

In 2020, she was crowned Miss World of Wheels at an international car show in Kansas City. This year, she earned the Fine Nine Award at the Starbird Show in Tulsa, the nation’s largest indoor car show. Other titles include Miss Rockabilly Ruckus in Ohio, Miss Shindig in Evansville, Indiana, and a crown in Branson, Missouri, at an event benefiting veterans.

These contests often serve charitable causes, from animal shelters to veterans’ organizations and children battling illness. To save money, Anderson sews her own outfits and creates props from car emblems and license plates, combining ingenuity with passion.

Looking Ahead to 2026
Anderson is eager to return to the Route 66 pageant on October 11, 2025. This time she’ll compete in her age bracket, but she dreams of reclaiming the national title as the Mother Road approaches its centennial in 2026.

“I would love to be part of the big birthday,” she said. “Last year I believed in myself when no one else did. I stayed in hostels, used public transit, even took out a small loan. This year I want to do it right and celebrate with the millions expected to travel Route 66.”

As a single parent with limited resources, Anderson hopes for sponsorships to help cover travel and wardrobe expenses. She envisions promoting vintage fashion, haircare, and makeup while completing the entire stretch of Route 66—an adventure she’s long dreamed of.

For those who want to support her journey, Anderson has set up a GoFundMe at: https://gofund.me/0e62945cb