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Brick row of rooms and the tall sign of the Munger Moss Motel, Lebanon, Missouri

State 2 of 8, driving west

Route 66 in Missouri: St. Louis, Cuba and the Ozarks

Missouri is the first state where Route 66 starts to curve and climb: a bent bridge over the Mississippi, stone motels in the Ozark hills, a river bend called Devils Elbow and the town where the number 66 was chosen.

Trips
5All cross state lines
Stops
5On our trips
Length
6 to 15 daysSmall groups
Best months
May to JunTrips run Apr to Oct
From
$2,190Per person

The Midwest: Illinois and Missouri

What the road is like in Missouri

After the flat run across Illinois, Missouri changes the mood of the road. Route 66 crosses the Mississippi at St. Louis, follows the old Manchester Road and I-44 corridor southwest, and climbs into the Ozark Plateau, a country of oak hills, caves, spring-fed rivers and small towns built around a courthouse or a rail depot. The road runs about 300 miles from the Chain of Rocks Bridge to the Kansas line west of Joplin, passing Stanton, Cuba, Rolla, Lebanon, Springfield and Carthage. Much of the old pavement survives as outer roads beside the interstate, and some of it, around Devils Elbow, still twists the way it did in the 1920s.

Five of our trips cross Missouri. The Illinois and Missouri section trip gives it the most time, about half the trip, and ends in Springfield. The End to End journey, the classic convertible and the motorcycle trip spend two days here, with a night at one of the restored 1930s and 1940s motels: the Wagon Wheel in Cuba or the Munger Moss in Lebanon, or similar. Main Street Museums slows down for the small towns, with an afternoon in Carthage. Darlene Moss leads most Missouri days, and on the full-route trips Ray Lindqvist stays with the group from Chicago to Santa Monica.

Route 66 tours through Missouri, 2026 and 2027

Per person sharing a double room. Trips that only cross part of Missouri are listed too.

All 16 trips

5 trips

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    Car club, family reunion or friends: any trip can run just for your group on your dates, from 6 travelers.

    Private and group trips

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    Save $150 per person on 2027 departures booked by January 31, 2027, plus last-minute prices on November and December 2026 dates.

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    Tell us how many days you have, the month and what you love: neon, diners, museums or open desert. A trip advisor in Tulsa suggests two or three trips.

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    5 stops

    Route 66 stops in Missouri

    Cyclists crossing the green steel trusses of the Chain of Rocks Bridge over the Mississippi

    St. Louis and the Chain of Rocks Bridge: A bridge with a bend

    Route 66 crossed the Mississippi on several bridges over the years, and the one people walk today is the Chain of Rocks Bridge, opened in 1929. It is about a mile long, with a 22 degree bend halfway across that drivers remembered for decades. Cars stopped using it in the late 1960s, and since 1999 it has been a path for walkers and cyclists. Our coach parks on the Illinois side, we walk out to the bend for the view of the two old water intake towers in the river, and walk back. In the city we pass the Gateway Arch, 630 feet tall, and finish at Ted Drewes on Chippewa Street, open since 1941, for a concrete: frozen custard so thick it is handed over upside down.

    • Walk to the bend of the Chain of Rocks Bridge
    • The Gateway Arch on the riverfront
    • A concrete at Ted Drewes Frozen Custard

    Best monthsApril to October

    Trips that stop here

    Row of stone motel cottages and a vintage car under shade trees in Cuba, Missouri

    Cuba, the mural city: Murals and a stone motel

    Cuba, about 80 miles southwest of St. Louis, calls itself the Route 66 Mural City and earns the name. Since 2001 local painters have covered downtown walls with more than a dozen scenes from the town's past, including Amelia Earhart's unplanned landing nearby in 1928 and a stop by Harry and Bess Truman on a 1953 road trip. The Wagon Wheel Motel, built in the 1930s from local Ozark stone, still rents its cottages, and several of our trips sleep there or in a similar motel. Up the road at Fanning, a rocking chair more than 40 feet tall stands outside the 66 Outpost. Earlier the same day we visit Meramec Caverns at Stanton, whose barn roof ads once lined the highway; the cave tour takes about 80 minutes.

    • Mural walk in downtown Cuba
    • A night at the Wagon Wheel Motel, or similar
    • Meramec Caverns at Stanton

    Best monthsApril to October

    Trips that stop here

    Big Piney River below wooded bluffs seen from the bridge at Devils Elbow, Missouri

    Devils Elbow: A river bend in the Ozarks

    Devils Elbow is a tight bend in the Big Piney River, and the old road drops down to it through oak woods; the name is said to come from timber raftsmen whose logs jammed here. The 1923 steel truss bridge, restored in 2014, is narrow, so our coach parks above and we walk down to the water. The Elbow Inn beside it opened in 1936 as the Munger Moss Sandwich Shop, before that name moved west to Lebanon, where the Munger Moss Motel, open since 1946, still lights its neon every night. Just up the hill is Hooker Cut, a rock cut about 90 feet deep blasted in 1945 to speed traffic to Fort Leonard Wood. Motorcycle riders love the curves on both sides of the river.

    • The 1923 Devils Elbow bridge
    • Hooker Cut on the four-lane 1945 alignment
    • Neon at the Munger Moss Motel in Lebanon

    Best monthsApril to June, September and October

    Trips that stop here

    Rows of restored classic cars inside the Route 66 Car Museum in Springfield, Missouri

    Springfield, Missouri: Where the number 66 was chosen

    Springfield has the best claim to be the birthplace of Route 66. On April 30, 1926, Cyrus Avery of Tulsa and Missouri's chief highway engineer, B. H. Piepmeier, sent a telegram from here proposing the number 66 for the new Chicago to Los Angeles highway. The Birthplace of Route 66 Roadside Park on College Street marks the story with murals and old signs. We visit the Route 66 Car Museum, a private collection of classic cars, and eat Springfield cashew chicken, a deep-fried version first served here in 1963. West of town at Paris Springs is Gary's Gay Parita, a 1930s Sinclair station rebuilt by the late Gary Turner. Our Illinois and Missouri trip ends here, with flights home from Springfield-Branson National Airport.

    • Birthplace of Route 66 Roadside Park
    • Springfield cashew chicken
    • Gary's Gay Parita Sinclair station

    Best monthsApril to October

    Trips that stop here

    Big white screen of the 66 Drive-In Theatre under blue sky in Carthage, Missouri

    Carthage and the 66 Drive-In: Courthouse, drive-in and Boots Court

    Carthage is a courthouse town of limestone and Victorian houses, and the 66 Drive-In Theatre on the west side is why our convertible trip stops. It opened in 1949, closed in the 1980s and reopened in 1998, and it still shows films on weekend nights in the warm months, with the old screen tower and speaker posts. The Jasper County Courthouse, a castle of local marble finished in 1895, anchors the square. Boots Court, a 1939 motel in the Streamline Moderne style, has been restored with its green neon trim. Just north of town, Red Oak II is a village of old buildings moved and rebuilt by the artist Lowell Davis. Our Main Street Museums trip spends an afternoon walking the square.

    • The 66 Drive-In Theatre
    • Jasper County Courthouse on the square
    • Boots Court Motel and its neon

    Best monthsMay to October

    Trips that stop here

    Coach, convertible or motorcycle

    Ways to drive Route 66 in Missouri

    1. By small coach through the Ozark towns

      The Illinois and Missouri trip and Main Street Museums travel in a 24-seat coach with no more than 14 guests and a professional driver. Darlene Moss plans the days around the stops that need time: a cave tour at Meramec Caverns, the murals in Cuba, the square in Carthage. Distances are short, rarely more than 120 miles a day, and every night is in a motel or hotel on the old road.

    2. By classic convertible on the curves

      Missouri is where Route 66 in a Classic Convertible starts to feel like a drive. Two guests share each restored 1960s convertible and swap the wheel when they like, with a mechanic in a chase truck behind. The Ozark outer roads roll and bend through woods and over creeks, and the day ends at a drive-in screen in Carthage or under the neon of a 1940s motel.

    3. By motorcycle to Devils Elbow

      On Route 66 by Motorcycle, Missouri gives riders the first real curves of the trip, from the hills past Rolla down to the Big Piney River at Devils Elbow and up through Hooker Cut. Riders are on rented Harley-Davidson touring bikes, the support van carries the luggage, and Hank Delgado sets a steady pace with fuel and coffee stops every hour or so.

    One price

    What is included on our Missouri trips

    In Missouri our multi-day prices cover motel and hotel nights (such as the Wagon Wheel in Cuba or the Munger Moss in Lebanon, or similar), breakfast every day, the dinners listed in each itinerary, the road captain and driver or convertible and chase truck, parking, and the entries named in the itinerary, such as the Meramec Caverns tour and the Route 66 Car Museum in Springfield.

    Flights are optional: each trip page shows the add-on price for flying into the start and home from the end, from 10 US cities. Full list and payments.

    Included on every Missouri trip

    • Restored vintage motels and good 3 to 4 star hotels, double room with private bathroom
    • Breakfast daily plus the lunches and dinners listed in the itinerary
    • A road captain from the first day to the last, and local guides at museums and parks
    • Small coach with a professional driver, or your classic convertible or motorcycle on themed trips
    • Museum, park and attraction entries listed in the itinerary
    • Airport pickup on day 1 and drop-off on the last day

    Seasons

    Best time to drive Route 66 in Missouri

    We run Missouri from April to October. April brings redbud and dogwood in bloom in the Ozark woods, though rain is common. May and June are green and warm, around 75 to 85 degrees. July is hot and humid, often over 90, so our one July departure keeps the outdoor stops in the morning. September and October are the best of the year: dry days, cool nights and, by mid October, the oaks and maples turning color along the river valleys around Devils Elbow.

    1. JanNo trips: No trips
    2. FebNo trips: No trips
    3. MarNo trips: No trips
    4. AprGood: Good
    5. MayBest: Best
    6. JunBest: Best
    7. JulGood: Good
    8. AugNo trips: No trips
    9. SepBest: Best
    10. OctBest: Best
    11. NovNo trips: No trips
    12. DecNo trips: No trips

    Best monthsGood, some trips runNo trips

    Practical

    Route 66 in Missouri at a glance

    • Route 66 miles

      About 300 miles from the Chain of Rocks Bridge to the Kansas line west of Joplin, along the I-44 corridor through St. Louis, Rolla, Lebanon and Springfield

    • Main towns on the road

      St. Louis, Eureka, Stanton, Cuba, Rolla, Devils Elbow, Lebanon, Springfield, Carthage, Joplin

    • Airports

      St. Louis Lambert (STL) in the east; Springfield-Branson National (SGF) in the southwest; Joplin Regional (JLN) near the Kansas line

    • Time zone

      Central Time, with daylight saving time from March to November

    • Road weather

      Spring is mild and wet, summer hot and humid, fall dry and colorful in the Ozarks; winter can bring ice on the hill roads

    • What to eat

      A concrete at Ted Drewes, toasted ravioli in St. Louis, Springfield cashew chicken, catfish and fried chicken in the Ozark towns

    • Best months for our trips

      May, June, September and October; April for spring blossom

    6 questions

    Route 66 in Missouri: questions

    How far is the walk on the Chain of Rocks Bridge?

    From the Illinois side parking to the bend and back is about a mile in total, flat and paved. The bridge has no shade and can be windy, so bring a hat. Anyone who prefers not to walk can wait by the coach, which keeps the bridge in view.

    Is the Meramec Caverns tour difficult?

    Not very. The guided tour takes about 80 minutes on lit, paved paths with some steps and slopes. The cave stays near 60 degrees all year, so a light jacket helps on a hot day. Guests who prefer to skip it can wait in the visitor area by the river.

    What are the old motels like inside?

    Small, clean and restored with care. The Wagon Wheel in Cuba and the Munger Moss in Lebanon, or similar motels, have private bathrooms, air conditioning and parking at the door, but no elevators, room service or gym. A night in a 1930s stone cottage shows you how travelers slept on this road before the interstates.

    Where does the Illinois and Missouri trip end?

    In Springfield, Missouri, after breakfast on day 6. Springfield-Branson National Airport (SGF) is about 15 minutes from the hotel, with connections through Chicago, Dallas, Charlotte, Atlanta and other hubs. We can book your flight home as part of the trip.

    Can we see a movie at the 66 Drive-In?

    The 66 Drive-In in Carthage shows films on weekend nights in the warm months. Our convertible trip and Main Street Museums stop there by day for photos, and when a departure lands on a show night we tell you in advance so you can stay for the film.

    Is Missouri hilly for a motorcycle beginner?

    The Ozark sections have curves and grades but nothing extreme, and the road surface is mostly good. Riders on our motorcycle trip need a valid motorcycle license and should be comfortable on a heavy touring bike before they arrive, since the bikes weigh around 800 pounds.

    Next on the road

    Keep driving from Missouri

    The whole route
    Ambler's Texaco, a small white station with two red pumps on Route 66 in Dwight, IllinoisRoute 66 in Illinois6 trips, from $249 Cracked deck of the white Brush Creek Rainbow Bridge near Riverton, Kansas, with a road shieldRoute 66 in Kansas5 trips, from $2,290 Pale yellow trusses of the Pony Bridge repeating over the Canadian River in OklahomaRoute 66 in Oklahoma7 trips, from $179

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    Drive Missouri on the old road

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