This post is the first in a seven-part series in the Vintage Camper Trailers Magazine. The “Begin Historic Route 66” sign. It’s more than a photo op—it’s the start of a journey that’s captured the imagination of travelers for nearly a century.
There’s something magical about standing at the corner of Adams Street and Michigan Avenue in downtown Chicago, staring up at the familiar red, white, and brown “Begin Historic Route 66” sign. It’s more than a photo op—it’s the start of a journey that’s captured the imagination of travelers for nearly a century. This stretch of highway represents both history and adventure, winding through small towns, classic diners, and wide-open Midwestern skies.
Chicago: The Official Start Line
Your adventure begins in the heart of Chicago, where the Mother Road was officially commissioned in 1926. Before hitting the highway, fuel up at Lou Mitchell’s Diner, a Route 66 institution known for its hearty breakfasts and complimentary donut holes. Just blocks from the starting sign, this family-run diner has been feeding travelers since 1923—a taste of Americana before you even leave the city limits.
Navigating out of Chicago with a vintage trailer can be a challenge, so plan your route carefully. Traffic is heavy, and not all exits are trailer-friendly. Chicago’s interchanges can be tight and confusing—study your route before departure.
Try leaving mid-morning to avoid rush hour, and follow the “Historic Route 66” signs as you make your way toward Joliet.
Rolling Through Route 66 Country
South of the city, the skyline gives way to small-town charm. In Joliet, stop at the Route 66 Welcome Center inside the old Rialto Square Theatre for maps, souvenirs, and local insights. A short drive farther south, Wilmington is home to the Gemini Giant, one of the most iconic “Muffler Men” statues along the route—a must-see photo stop that perfectly captures Route 66’s quirky roadside appeal. Fuel up often. Gas stations thin out between smaller towns.
Continue on to Pontiac, Illinois, a small town that has wholeheartedly embraced its Route 66 heritage. The Pontiac Route 66 Hall of Fame and Museum features vintage cars, memorabilia, and a mural-covered downtown that’s a photographer’s dream. Don’t miss the Route 66 shield painted on the street, perfect for a snapshot of your trailer proudly parked on history.
Springfield: A Capital Stop
As you approach Springfield, the Illinois capital, you’ll find plenty of vintage-friendly RV parks and campgrounds, like the Double J Campground, which welcomes classic rigs. Springfield is a fitting first destination—Abraham Lincoln’s hometown and a city where the old and new sections of Route 66 meet. Visit Cozy Dog Drive In, birthplace of the original corn dog, still operated by the founder’s family.
