Where Route 66 History Meets the Road

THE ITINERARY AT A GLANCE

This three-day Springfield, Illinois adventure celebrates the heart and history of Route 66, blending classic Americana with rich cultural storytelling.

For more great stories about Route 66, check out our Route 66 Tour Planner

Springfield Day-to-Day Itinerary

Day 1: Murals and excellent exhibits

Arrive in Springfield and, after getting your bearings, enjoy a delicious lunch at Maid-Rite Sandwich Shop. This is the first drive-thru restaurant in the country. Opened in 1924, your group can savor a loose-meat burger with homemade root beer.

Afterward, at your leisure, explore Route 66 and its many incredible murals and wayside exhibits featuring 20+ great photo ops and a slew of fun. Later, check into your hotel and relax a bit before savoring dinner at Vondra Social House on the edge of the Lincoln Home neighborhood.

For more great stories about Route 66, check out our Route 66 Tour Planner

Day 2: Abraham Lincoln Presidential Museum and more

Start your day with a trip to the Abraham Lincoln Presidential Museum. Experience history like never before when you step inside key moments in Lincoln’s life, from triumph to tragedy. Explore immersive displays and shows that drive home the human costs of slavery and war. Connect with Lincoln and his family through artifacts that can’t be found anywhere else in the world. You’ll feel like you’re walking in Lincoln’s shoes.

Next, enjoy lunch at Motorhead’s Bar & Grill. Motorhead’s is more than just a restaurant and bar–it’s a tribute to the legendary Route 66 and vibrant culture that surrounds it. The walls come to life with vintage memorabilia, photographs and artifacts, each telling a story. It’s a great spot for lunch with your tour group.

For more than 85 years, the Ace Sign Museum has been a family-owned, actively operating sign company. They have now opened their facilities to showcase a remarkable collection of historic signs from Springfield and Route 66. This tour is guided.

Take a quick picture, stop at Shea’s Gas Station, owned and operated by Bill Shea for 50 years; this piece of Americana still holds true to its roots. Then, head to the Route History Museum, which integrates history and technology through exhibits, storytelling and a virtual reality experience that highlights the significant roles of Black businesses, the Great Migration, and sundown towns along the Illinois leg of Route 66 during the Civil Rights and Jim Crow eras.

Freshen up at your hotel before dinner at Maldaner’s. Established in 1884, Maldaner’s is one of Springfield’s finest restaurants and the oldest restaurant on Route 66.

End your day with a visit to the Route 66 Experience at the Illinois State Fairgrounds. This experience offers a breathtaking birds-eye view of Illinois’ legendary Mother Road. Showcasing 92 communities from Chicago to the Chain of Rocks Bridge, step back in time with billboards and muffler men who once lined the famous route. Best enjoyed in the evening when the neon comes to life.

Day 3: Take a beautiful walk along the original Route 66

Take a morning stroll along one of the original segments of Route 66. Nestled beside the Sangamon River, this quarter-mile stretch of road has been hidden away, untouched and overgrown, for nearly 90 years. Initially part of the original stretch of Route 66, this segment was only in use for about a decade before the highway’s alignment changed. This site recently reopened as a walking exhibit offering visitors the chance to learn about its history through interpretive signage, old-fashioned billboards, and Burma Shave signage. As visitors stroll along the original pavement, they’ll be stepping back in time to experience a slice of history frozen in place.

Next, make a stop at the Bob Waldmire Route 66 Art Exhibition, which is being held only in 2026. Known for meticulous attention to detail, Springfield native Bob Waldmire created extremely detailed maps of Route 66. His work is celebrated for the nostalgia and culture of Route 66. His art is on display at The Pharmacy until December of 2026.

For lunch, stop at the famous Cozy Dog Drive-In. Inventers of the original hot dog on a stick, Cozy Dog has been serving the public for over 70 years and still use the same batter recipe that Ed Waldmire developed back in 1946.

Headed out of town so soon? Travel down a stretch of the original Route 66Brick Road. Located in nearby Auburn, it’s just a 20-minute drive south from Springfield.