How to enjoy five days on Route 66 in Missouri

Experience absolute freedom while cruising along Missouri’s scenic portion of Route 66 with this 5-day itinerary

By Erika Ebsworth-Goold

Located in America's heartland, Missouri has old-school Americana, quirky small towns and surprising natural wonders in spades.

A leisurely cruise up Route 66 is one of the best ways to truly get to know the state. The beloved highway’s centenary is coming up in 2026, so now is the perfect time to plan an epic “get your kicks” road-trip across Missouri.

Scroll down for the perfect 5-day itinerary, cruising from Joplin to St. Louis, including many of the cultural, natural, and historic highlights you won’t find anywhere else but the Show-Me State.

Day 1: Joplin and Springfield

Your tour starts in the southwestern city of Joplin. Start at the Joplin History & Mineral Museum. After a visit here, you’ll better understand the town’s backstory, from its mining roots to its brush with Bonnie and Clyde. The infamous couple hid out in town and got into a shootout with police after one of their heists in the 1930s.

For a culture fix, the Spiva Centre for the Arts has you covered with exhibits spanning quiltwork to photography, often from local artists.

If the great outdoors is more your speed, get to Grand Falls, the largest continuously running waterfall in Missouri, or stretch your legs with a hike of the arid glade ecosystem at Wildcat Glade Natural Area just south of the city.

A recommended pit stop

On your way out of town, make a pitstop at Route 66 Mural Park. Its two large tile murals depict classic highway scenes and includes a replica of a 1964 Corvette.

Heading east

Heading east from Joplin, you’ll soon hit the small town of Carthage. Known as the Maple Leaf City, Carthage boasts several Route 66 attractions, including the 66 Drive-In Theatre and the Boots Court Motel, built back in 1939 specifically for road-trippers.

For true Americana kitsch, swing through Red Oak II. This colourful hamlet was recreated by artist Lowell Davis and modelled after the real town of Red Oak where he grew up.

Spend the night in Springfield

The town of Spencer and Gary’s Gay Parita—a nostalgic, old-time filling station—are both worth quick pull-overs as you progress toward Springfield, about 88km up the road.

After a terrific dinner at Black Sheep Burgers & Shakes, plan to hang your hat at the Hotel Vandivort, a sleek and chic boutique hotel in the heart of the city. For an authentic Route 66 experience, spend the night at the Best Western Route 66 Rail Haven. The motor court, built in 1938, features eight original sandstone cottages and an Elvis-themed suite where “The King” once stayed.

Day 2: Springfield, Lebanon, Pulaski County, Rolla

Start your day at the College Street Café. This joint’s been serving gut-buster breakfasts for decades, and the slinger, a happy mess of hashbrowns, eggs, chilli and cheese is a local favourite.

Get your motor really running at the Route 66 Car Museum, where you’ll find more than 60 classic vehicles displayed in a garage-style space. The History Museum on the Square gives a glimpse of local heritage, from when Native Americans first inhabited the area through to the heyday of Route 66. 

For lunch, stop along the Cashew Chicken Trail. The beloved takeout classic was created here by Chinese immigrant David Leong in the 1950s; dozens of area restaurants now serve the dish, and you can easily find them on the newly created online trail.

Head to Rolla

After lunch, head east toward Rolla, an easy 177km stretch. Along the way, take a break at the Lebanon-Laclede County Library’s Route 66 Museum, where you’ll trip back in time viewing artefacts mimicking a 1950 roadside motel.

Pass through Pulaski County, with its variety of explore-worthy spots: the square in downtown Waynesville features cute cafes and shops, the Route 66 Neon Park in St. Robert showcases neon signs once used along the highway, and the Uranus Fudge Factory is a necessary stop for any sweet-tooth.

Venture across Devil's Elbow Bridge

As you cross Devil’s Elbow Bridge, keep in mind the truss structure was built over the Big Piney River back in 1923 and was restored by Route 66 activists in 2013.

Rest in a cosy cottage

Just outside Rolla, check into the Prairie Base’s Blackberry Room, a beautifully appointed cottage on a working dairy farm.

Day 3: Rolla, St. James, Cuba, Pacific, Eureka

Day three of your Missouri Route 66 road trip sees you heading to the outer St. Louis suburbs, with plenty of exciting diversions in between.

Before you leave Rolla, hit the Missouri University of Science and Technology campus to see its impressive half-scale replica of Stonehenge, carved from 160 tonnes of granite with water-jet technology developed at the school.

Fifteen minutes up the road, you’ll hit St. James. The town was first settled by iron miners, but Italian immigrants later found the land was ideal for producing grapes. Today, several wineries can be found in and around the town. St. James Winery produces award-winning varieties; if beer is more your scene, head right next door for craft ales at the Public House Brewing Company.

Venture to Cuba

A bit further east, in the town of Cuba, you’ll find a roadside attraction of epic proportions: a 4.2m-tall rocking chair that once held a Guinness World Record. Cuba also has many colourful murals, depicting the people and spirit of Route 66.

Grab a bite to eat at Missouri Hick Bar-B-Que or Shelly’s Route 66 Café to fill up before cruising past the historic Wagon Wheel Motel – the oldest continuously operating motel on Route 66 – on your way out of town.

Delve into Missouri's caves

If you’re in the mood for an underground adventure, Stanton’s Meramec Caverns (the largest cave complex in the state) is known as Missouri’s greatest buried treasure and stays at a constant, cool 14.5 degrees.

The Red Cedar Inn in Pacific is a time capsule of Route 66 history, listed on the National Register of Historic Places. While it no longer serves its famous fried chicken, it’s been restored as a pit stop with information all about the Mother Road.

Experience a Eureka moment

Just a stone’s throw away, Eureka’s Route 66 State Park along the Meramec River has a great visitor’s centre and is the perfect place to get in a few steps along meandering park trails.

Another half hour up the road and you’ll arrive in St. Louis; the Angad Arts Hotel offers weary travellers quirky, fun rooms and suites in the colour that suits their mood! Blue is for embracing freedom while yellow is about sparking curiosity. Red is to ignite a sense of empowerment and green is for a sense of rejuvenation.

Day 4: St. Louis

Wake up in the Gateway of the West with a wander through one its most peaceful spots, the Missouri Botanical Garden.

Founded in 1859 by British immigrant Henry Shaw, the garden and its herbarium include more than 6 million specimens. Guided walking tours and narrated tram tours offer insight on the garden’s many features, including the Climatron® and Japanese Garden. No matter what time of year you visit, something’s bound to be blooming in striking colour.

Head to Forest Park

Next up, take a quick zip west and explore everything Forest Park has to offer. One of the largest urban parks in the US, it houses the Saint Louis Art Museum, Saint Louis Zoo, Missouri History Museum and the Saint Louis Science Center. If you’re visiting during the summer, plan to take in an evening show at the Muny, America’s oldest and largest outdoor musical theatre.

Indulge your taste buds

St. Louis has a rich and developing foodie scene; you really can’t go wrong with any choice. Fans of Italian cuisine should head to the Hill, while all sorts of authentic international flavours can be found in the city’s South Grand district. BBQ lovers will want to sample Salt and Smoke, Sugarfire and Pappy’s Smokehouse; all are award-winning spots known for their pork, chicken, and brisket.

And don't forget your sweet tooth

For a St. Louis classic dessert, detour to Ted Drewes. Locals love their famous frozen custard concretes, shakes loaded with delicious mix-ins, spun so thick you can turn them upside down without an unfortunate spillage. Pro-tip: you can’t go wrong with the Cardinal Sin, topped with cherries and doused in hot fudge!

If you’ve room left, grab a classically crafted nightcap at The Gin Room, named a 2023 James Beard semi-finalist for Outstanding Bar.

Day 5: St. Louis

Plan to start your day downtown with a history fix. Take an early stroll (or jog!) along the greenspace in the Gateway Arch National Park and get a glimpse of the nearby Eads Bridge.

Built 150 years ago and the oldest surviving bridge over the Mississippi, it’s a true engineering triumph. Its foundations, more than 30m below water level, were the deepest underwater constructions at the time. While currently closed for renovations, the Old Courthouse – set to open in Spring 2025 – is also worth a peek.

It’s here where an enslaved man, Dred Scott and his wife Harriet sued for and were granted their freedom, only to have the ruling overturned by the U.S. Supreme Court. It was a decision that helped plunge the nation towards Civil War.

Trundle by tram

Next up, check out the Museum at the Gateway Arch. Located underground beneath the legs of the Arch, the free showcase gives you an additional perspective about the city’s past and present.

Finally, it’s time to hop on a tram for a brief ride to the top! You’ll be rewarded with sweeping views of downtown and the Mighty Mississippi from the apex of the 192m monument.

Learn about Missouri's brewing traditions

St. Louis also has a long and proud brewing tradition. To learn more about the beermaking process, your next stop takes you a few kilometres south of downtown for a tour at Anheuser-Busch Brewery. Here, you’ll learn all about St. Louis’s original beer barons, see how the suds are made, and even get to give them a taste. Be sure to say hello to the world-famous Budweiser Clydesdales; a few of these majestic horses live onsite in a special stable.

Marvel at cultural highlights

Marvel at the beauty of the Cathedral Basilica of St. Louis, which houses one of the largest mosaic collections in the world. To lean even more into the Route 66 theme, consider a stop at the National Museum of Transportation, dedicated to America's love of rail and transit.