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22. BROOKS CATSUP BOTTLE( COLLINSVILLE): One of the most famous roadside landmarks in America – a giant ketchup bottle water tower built as a promotional symbol that became a Route 66 icon.
MISSOURI
23. CHAIN OF ROCKS BRIDGE( ST. LOUIS): A famously curved bridge that once carried Route 66 traffic across the Mississippi River, now a pedestrian landmark with sweeping river views.
24. GATEWAY ARCH( ST. LOUIS): An iconic 630- foot monument symbolizing westward expansion, just a short detour from the historic Route 66 alignment.
25. TED DREWES FROZEN CUSTARD( ST. LOUIS): A legendary Route 66- era custard stand known for its ultra- thick“ concrete” frozen desserts served roadside.
26. ROUTE 66 STATE PARK( EUREKA): A preserved stretch of old Route 66 featuring interpretive exhibits, trails, and remnants of the original highway.
27. MERAMEC CAVERNS( STANTON): A massive cave system heavily promoted by vintage Route 66 billboards, famously linked to Jesse James folklore.
28. WAGON WHEEL MOTEL( CUBA): One of the oldest continuously operating motels
on Route 66, known for its beautifully preserved stone cabins.
29. SHELLY’ S ROUTE 66 CAFE( CUBA): A nostalgic diner serving classic roadside fare in the heart of Route 66 mural country.
30. CUBA MURALS( CUBA): A series of vibrant outdoor murals depicting local history and Route 66 culture throughout downtown.
31. ROUTE 66 NEON PARK( ST. ROBERT): This outdoor, open- air museum features restored, vintage neon signs that originated along Historic Route 66.
32. DEVIL’ S ELBOW BRIDGE( DEVIL’ S ELBOW): A dramatic curve along the Big Piney River that once challenged early Route 66 travelers with its sharp bends and scenic beauty.
33. FANNING 66 OUTPOST( FANNING): A quirky roadside stop featuring souvenirs and Route 66 memorabilia.
34. RED ROCKER( FANNING): One of the world’ s largest rocking chairs, a bold and playful Route 66 photo stop.
35. STONEHENGE REPLICA( ROLLA): A scaleddown replica of England’ s Stonehenge, built as a quirky roadside attraction near Route 66.
36. URANUS FUDGE FACTORY AND GENERAL STORE( URANUS): A famously cheeky Route 66 stop known for its novelty humor, quirky gift shop, and homemade fudge – built around playful roadside branding that makes it one of the most talked- about and photographed attractions in Missouri.
37. MUNGER MOSS MOTEL( LEBANON): A neonlit Route 66 icon and one of the most photographed motor courts on the entire highway. As of this article’ s publishing, the hotel is closed, but visitors can still stop to check out the sign.
38. MISSOURI ROUTE 66 MUSEUM( LEBANON): A museum preserving artifacts, stories, and memorabilia from Missouri’ s Route 66 heritage.
39. GILLIOZ THEATRE( SPRINGFIELD): A beautifully restored 1920s theater that once served Route 66 travelers with live entertainment and film.
40. ROUTE 66 CAR MUSEUM( SPRINGFIELD): A collection of vintage automobiles celebrating the golden age of American road travel.
41. RED’ S GIANT HAMBURG( SPRINGFIELD): Home of the world’ s first drive- thru restaurant, revived as a Route 66 landmark.
42. ROUTE 66 DRIVE IN THEATER( CARTHAGE): A classic outdoor cinema that preserves the mid- century drive- in experience for modern Route 66 travelers.
44 / AUGUST 2026 / RIDERMAGAZINE. COM