Celebrate 100 Years of Route 66 in Lemont: The 100-Mile Road Trip
This November, the U.S celebrates the 100th anniversary of Route 66. Lemont Downtown was here for Route 66’s earliest days—a newly uncovered historical map confirms what locals suspected: Downtown Lemont was part of the original Route 66. This summer, we’re encouraging everyone to take part in the 100 Year Road Trip, celebrating the most iconic towns along the first 100 miles of Route 66.
Our Spot on the Mother Road
The I&M Canal put Lemont on the map, helping move goods and people. The development of the Pontiac Trail and Highway 4, which ran from Chicago to St. Louis, made Lemont a natural choice for the alignment of the historic Route 66. Followers of the original Route 66 could stop in Lemont to grab a beer at Tom’s Place (yes, it was here back then!) or to patronize businesses along Main Street. In 1928, Route 66 was realigned to avoid railroads and winding streets, but historians still attribute the original route to Lemont.
“Transported: The Original Detour” by Rob Moriarty
To celebrate the 100th anniversary of Route 66, the most iconic 40 towns across the first 100-miles have partnered with local artists to create custom car benches that celebrate local history, culture, and hidden gems.
Rob Moriarty, a local artist and educator known for his work on the LeMontsters, was selected to craft the bench for Lemont. The 1972 Chevrolet bench is full of colorful limestone features, including the seven steeples, the I&M Canal, and the distant Chicago skyline.
Residents and visitors are encouraged to sit and take photos while at events this summer.
The Best Detour
There is plenty to do in Lemont Downtown on an average day, but especially this summer. Plan your Historic Route 66 road trip from Chicago’s Navy Pier (or the original start near The Art Institute) and plan on spending time in Lemont shopping, dining, or learning more about local history. Here are a few of our favorite things to do:
Have a Full Lemonty Beer at Pollyanna Brewing or keep it old school with a Schlitz at Tom’s Place. Pollyanna Brewing Co is an award-winning brewery known for its festive IPAS and Lagers and the distilled spirits at nearby Pollyanna Social. Pop over to Tom’s Place, one of the oldest bars in Lemont that serves icy cold Schiltz beer on tap.
Grab an entire pie at Wooden Paddle or keep it old school with a burger at Nick’s Tavern. Wooden Paddle was voted best pizza in the Chicago West Region, and Nick’s was voted best burger in all of Chicago. Grab a seat and see for yourself.
Find a hidden treasure at Mabel’s Market or keep it old school with a trip to Oakridge Toys & Hobbies. Stop by Mabel’s to find vintage furniture and home goods, and find a new puzzle, toys, or invest in a new hobby at Oakridge.
Live like a local with a walk on the Quarry or a run through the hills of Lemont. Stop by during our Lemont Cruise Nights and Sunset Soirees to get a feel for how all of the locals live.
No matter where you get your kicks, we hope you stop by Route 66 and experience the magic of Lemont on the Great American Road Trip.

