Charming Small Towns Along Route 66 in Illinois, Missouri and Kansas

Stretching over 3,800 kilometers from the picturesque shores of Lake Michigan in Illinois to the stunning Pacific Ocean in California, the legendary Route 66 highway brings together the past and present. Feel the sense of adventure that Route 66 has been providing for generations on a nostalgic road trip highlighting quaint towns filled with rich history, striking landscapes and historic landmarks. Fly into either of Chicago’s international airports – O’Hare (ORD) or Midway (MDW) – and rent a car to start this unforgettable road trip. 

Joliet, Illinois: Entertainment Capital Linking Yesterday and Today

Make time to explore Chicago, an international hub for world-class museums, tasty food and can’t-miss attractions. Take a photo of the new Route 66 sign at Michigan Avenue and Adams Street in front of the Art Institute of Chicago – the official starting point of the iconic roadway.

Head southwest to Joliet, Illinois, a gem on the outskirts of the Chicago metropolitan area. At the Joliet Area Historical Museum, uncover the city’s history by admiring memorabilia and vintage collectibles in the Route 66 Experience exhibit.

Nearby, tour the Old Joliet State Prison, a penitentiary that opened in 1858 and remained active for the next 144 years. Guides can tell you historic and spooky stories of the landmark while pointing out filming locations you might recognize from the movie The Blues Brothers and the television show Prison Break. Check out the performance schedule of the Rialto Square Theatre in downtown Joliet. The opulent vaudeville movie palace from the 1920s now hosts concerts, movie screenings, comedy shows and ballet performances. For some more excitement, head to one of Joliet’s two Vegas-style resorts for gaming, elevated dining options and live shows.

Bloomington, Illinois: Attraction-filled Destination for the Whole Family

Jump into your car and continue on the Mother Road to Bloomington. Make a pit stop on the way in Pontiac to visit the Route 66 Association of Illinois Hall of Fame and Museum, making sure to snap a photo of the world’s largest Route 66 Sign Mural painted on an exterior wall. Appreciate the large collection of classic cars at the Pontiac Oakland Auto Museum around the corner.

Bloomington is a college town with family-fun spots and strong ties to Abraham Lincoln. Visit the Crusin’ With Lincoln Visitors Center housed in the historic courthouse downtown where Abraham Lincoln worked as a young lawyer. The center’s exhibits highlight the area’s fascinating past, from the life of the famous president to the history of Route 66. Bring the kids to the Prairie Aviation Museum to wander around its aircraft collection and aviation-themed exhibits. Enjoy carnival rides at Grady’s Family Fun Park, explore three floors of hands-on exhibits at the Children’s Discovery Museum and see all your favorite animals at the Miller Park Zoo before continuing on the Mother Road.

Granite City, Illinois: Hidden Gem with Creative and Open-air Treasures 

The next stop takes you to Granite City, a charming town on the Mississippi River at the border of Illinois and Missouri. Stretch your legs on the way at Route 66-themed stops like Route 66 Legends Neon Park in Springfield, Ariston Café in Litchfield and the West End Service Station in Edwardsville. Just before arriving in Granite City, take a brief detour to see the Old Chain of Rocks Bridge. This was the original bridge that took drivers across the mighty Mississippi when cruising Route 66, now only open to pedestrians. Walk the Eagle Points Trail along the Chain of Rocks Canal to Eagle Point for views of St. Louis, Missouri, or stroll the Madison County Transit Confluence Trail, 33 kilometers of mostly paved paths along the Mississippi levee system.

Head to downtown Granite City for dining options and surprising artistic experiences. Wander the Granite City Art & Design District, a revitalized area of warehouses with colorful murals, outdoor sculptures, gardens and art galleries. Rest up at local hotels or enjoy the great outdoors at several campgrounds in the area.

Cuba, Missouri: Small Town with a Big Sense of Adventure

Start the day driving across the Mississippi River to the next state in this road trip, Missouri. You will enter through St. Louis, a global city overflowing with attractions and culinary delights. Head to the top of the iconic Gateway Arch, the symbol of westward exploration and the tallest human-made monument in the USA. Forest Park is a public green space with an art museum, zoo, science center with a planetarium and history museum – all with free admission.

Continue driving Route 66 to reach the quaint town of Cuba. Make a stop on the way to explore Meramec Caverns, a perfect natural attraction to welcome you to Missouri’s cave country. Wander Cuba’s cute downtown packed with over 15 murals depicting scenes from local and national history.

See Route 66 memorabilia among other displays at the Crawford County Historical Society & Museum, and get active outside at Meramec Spring Park. The park offers hiking trails for every skill level, a trout hatchery, two museums, playgrounds and picnic spots. Rent a canoe or kayak for adventure along the pristine Meramec River. Nearby, explore underground paths with a guide at Onondaga Cave State Park or take to the many walking paths found above ground. Sit back and take in spectacular Missouri countryside views and handcrafted wines at Peaceful Bend Winery. 

Lebanon, Missouri: Outdoor Bliss along the Mother Road

Cruise along lush woodlands, rugged hills and scenic bluffs of the Mark Twain National Forest to Lebanon. The town is a great basecamp for exploration of the Ozark Plateau, a mountain range filled with outdoor recreation options, distinct wildlife and nonstop scenic views. Mother Road enthusiasts will love exploring Lebanon’s Route 66 Museum. Find a recreation of an old gas station and a classic diner among other Route 66 memorabilia and displays that fill the space. Shoppers can’t miss the Antique Trail to browse shops selling rare collectibles, vintage clothing and more.

Spend some time in Historic Downtown Lebanon, which blends nostalgic charm with modern breweries, cafés and local shops. The town offers a varied collection of lodgings, including budget-friendly hotels and rentable cottages. Bennett Spring State Park is nearby, offering hiking trails, cabins for overnight stays, fly fishing lessons and a nature center. Explore other state parks just north of Lebanon, like Lake of the Ozarks, Ha Ha Tonka and Pomme de Terre, then relax for the night in one of a variety of lodging options, including budget-friendly hotels and cottage rentals.

Springfield, Missouri: “Birthplace of Route 66” & a History Buff’s Dream

The next stop, Springfield, combines warm hospitality with an eclectic collection of attractions. On the way, enjoy quirky destinations like the Redmon’s Candy Factory in Phillipsburg, the Missouri Rt. 66 Welcome Center in Conway and the Hubble Space Telescope Replica in Marshfield. If you enjoy a good spook, take a haunted tour at night of Springfield’s Pythian Castle, where some believe spirits from the past linger. Daytime tours are more traditional, focusing on the history of the landmark, built in 1913 as an orphanage before becoming a prisoner-of-war camp during World War II.

Get your kicks at Route 66-related spots like the Route 66 Car Museum, with a large collection of vintage and classic automobiles, and the History Museum on the Square, which houses six permanent galleries dedicated to different periods in Route 66 history. Walk among stalagmites and stalactites at Crystal Cave, which has been open for tours since 1893. Other can’t-miss attractions in Springfield include the Air & Military Museum of the Ozarks, Bass Pro Shops Motorsports Museum, Wonders of Wildlife National Museum & Aquarium and the site of the American Civil War Battle of Springfield.

Galena, Kansas: Picturesque Community with Quirky Photo-ops and Landmarks

Before you leave Missouri, stop to snap photos at the Route 66 Mural Park in Joplin, Missouri. The final stop of the trip takes you to the small, but can’t-miss, section of Route 66 that cuts through Kansas. Spend some time in Galena, a small town with some deep local history. Dive into local lore, including how Galena inspired the Pixar film “Cars,” at the Galena Mining & Historical Museum housed in the town’s former railroad depot. Take photos with “Cars” characters at roadside attraction Cars on the Route, then see Route 66 giants at Gearhead Curios, both a short walk down Main Street from the museum.

On the way to your next stop, cross the historic Rainbow Bridge outside of Riverton, the only surviving Marsh arch bridge of Route 66 is still crossable by car. Take time to explore Baxter Springs, a nearby town whose heritage center highlights Native American, colonial and Route 66 history of the area. If your Mother Road journey ends here, drive about an hour and a half south to Tulsa, Oklahoma, to catch a flight from Tulsa International Airport (TUL). You can also drive about two and a half hours north to Kansas City, Missouri, and fly out of Kansas City International Airport (MCI). If you plan to continue your Route 66 road trip beyond Oklahoma, you’ll find over 2,000 kilometers of wonders and Americana to explore before reaching its end in Santa Monica, California.