Route 66 in Missouri is a journey through the heartland of America. This iconic highway weaves from St. Louis to the Kansas state line, and through the picturesque Ozark Mountains. Befitting the moniker ‘Main Street of America’ it courses through small villages that appear to have been lifted from Norman Rockwell prints.

Sharing America’s tory. Inspiring road trips by telling people where to go. It’s what we do at Jim Hinckley’s America.

So, join us on a journey through some of the most captivating sites along Route 66 in Missouri, with insights from Elizabeth Olwig of the Route 66 Association of Missouri, the guest on the January 5, 2025, episode of Coffee With Jim. During our conversation Olwig shared insights into how a new generation of enthusiasts view Route 66 and historic preservation. She also discussed the association’s centennial initiatives and talked about projects currently under development.

Route 66 Association of Missouri

The Route 66 Association of Missouri has assumed a leadership position in preserving the legacy of this historic highway in the Show Me State. Their efforts ensure that into the highways centennial and beyond, future generations can experience the magic of Route 66.

For more information, visit the Route 66 Association of Missouri’s website.

Author Joe Sonderman

On the podcast Olwig also talked about the many contributions of renowned author Joe Sonderman. In addition to his work with the Route 66 Association of Missouri that includes serving as the editor of its official publication, he is a renowned radio personality in St. Louis.

Joe’s extensive work has shed light on rich history and vibrant stories along Route 66. His books are a treasure trove of information. As a result, Sonderman is a popular speaker in the Route 66 community.

Cuba, Missouri

My dearest friend and I have a soft spot for Cuba. There is just something comforting about this little village where most folks treat you like an old friend.

Known as the “Mural City,” Cuba, Missouri, is a must-visit destination along Route 66. The Wagon Wheel Motel, one of the oldest continuously operating motels on the highway, offers a nostalgic experience with its charming accommodations. The city’s vibrant murals depict historical events and local culture, making a stroll through the historic heart of Cuba an artistic journey.

Cuba is also home to a variety of delightful restaurants. Counted among our favorites are Shelly’s, Weir on 66, Huddle House, and Frisco’s. So, be sure to indulge in local cuisine and wrap up a day of Route 66 adventure with a restful night’s sleep at the Wagon Wheel Motel.

Side Trips

– **Steelville, Missouri:** Just a short drive from Cuba on highway 19, Steelville is a haven for outdoor enthusiasts. The town offers scenic river floats, hiking trails, and charming shops as well as a time capsule business district.

– **Meramec Springs State Park:** This park is a natural wonder with crystal-clear springs, abundant wildlife, and picturesque landscapes. It’s an ideal spot for a relaxing day in nature.

These are two side trips I highly recommend for anyone staying overnight in Cuba.

Birthplace of Route 66 Festival in Springfield, Missouri

An event or festival will add some zest to any Route 66 odyssey. The ultimate Route 66 festival takes place every summer in Springfield.

The Birthplace of Route 66 Festival regularly attracts tens of thousands of visitors. The festival features live music, classic car shows, and a variety of vendors offering Route 66 memorabilia. Attracting enthusiasts from all over the world, this event is a destination in itself.

Red Oak II

Red Oak II is a unique, artistically recreated village founded by folk artist Lowell Davis. This enchanting site is a portal into the past. Its meticulously restored buildings exude vintage charm. It’s a testament to the spirit of Route 66 and to the preservation of American heritage.

Gasconade Bridge Preservation Project

The preservation of the Gasconade Bridge is a significant undertaking by the Route 66 Association of Missouri. This historic bridge, an architectural marvel, has been saved from destruction by the association. Efforts to preserve such landmarks are crucial in maintaining the idiosyncratic nature of Route 66.

Meramec River Bridge Restoration

Olwig shared some exciting news on the podcast. Work is also underway to restore the Meramec River Bridge at Route 66 State Park. This project aims to revive another important piece of Route 66 history in time for the highway’s centennial.

Eads Bridge History

Our conversation also touched on the numerous Mississippi River crossings at St. Louis. Often overlooked the historic Eads Bridge Is the only one of these bridges not used by Route 66.

This bridge is a historic landmark. Built in the 1870s it is the oldest iron bridge in the United States.

National Museum of Transportation

The National Museum of Transportation west of St. Louis is a surprisingly obscure attraction. This too was the subject of discussion on the podcast.

The museum houses an astounding collection of historic vehicles and transportation artifacts. From vintage automobiles to locomotives, the museum offers a comprehensive look at the evolution of transportation in America. It also preserves the extensive history of the auto industry in St. Louis.

Automotive History in St. Louis

St. Louis boasts a rich automotive history. The revitalization of the historic auto row district just a few blocks off Route 66 is breathing new life into the city’s industrial heritage. This area, once bustling with car dealerships and factories, is now a vibrant community of restaurants, coffee shops, and microbreweries.

Shamrock Court Restoration in Sullivan, Missouri

Counted among the many exciting developments along Route 66 in Missouri is the ongoing restoration of Shamrock Court in Sullivan, Missouri. Volunteers that donate labor and time to the project are a testament to the dedication of Route 66 enthusiasts. This historic motel is being meticulously restored to its former glory, preserving its unique architectural features and nostalgic charm.

Trailnet and Chain of Rocks Bridge

Trailnet, a nonprofit organization, is dedicated to creating healthy and active communities through biking and walking initiatives. One of the notable landmarks in this trail system is the Chain of Rocks Bridge.

This beautiful old bridge built in the 1920s was initially a toll road for travelers looking to bypass the congestion of St. Louis. For a similar reason it was incorporated into the course for Route 66 in about 1930.

Plan Your Route 66 Adventure in Missouri

Missouri’s segment of Route 66 is a treasure trove of historical landmarks, natural beauty, and cultural attractions. Whether you’re exploring the artistic murals of Cuba, marveling at the engineering feats of the Eads Bridge, or immersing yourself in the automotive history of St. Louis, there’s something for every traveler to enjoy.

For more information and to plan your Route 66 adventure, visit the Route 66 Association of Missouri’s website. Don’t forget to tune in to “Coffee With Jim” on Podbean every Sunday morning for fascinating interviews and updates about Route 66.