My Favorite Route 66 Stops Across Three States
There is something about Route 66 that makes me want to pull over every few miles.
An oversized pink elephant? Absolutely. A historic water tower shaped like a catsup bottle? I’m stopping. A colorful mural tucked into a small town? That is exactly my kind of detour.
In June 2026, my brother Craig and I explored portions of historic Route 66 through Illinois, Missouri and Oklahoma during our eight-day Midwest road trip.
We weren’t trying to drive every mile of the Mother Road. Instead, we focused on interesting attractions, roadside Americana, quirky landmarks, historic places and photography opportunities.
Some of our favorite discoveries were planned. Others happened because something caught our attention along the highway and we decided to investigate.
Roadside Americana, Historic Places & Unexpected Detours
These are my favorite Route 66 stops across three states, with firsthand impressions, photography tips and practical information to help you plan your own adventure.
Looking for our actual driving route, hotels and daily activities? Read my 8-Day Midwest Road Trip Itinerary →
You can also explore The Ultimate Midwest Road Trip → for more highlights from our adventure.
Disclosure: Pink Elephant Antique Mall hosted our lunch and provided a preview of its Haunted School during our visit. Other hosted experiences from the broader Midwest road trip are disclosed in the corresponding articles. All opinions and photographs are my own, and no positive coverage was guaranteed.
What Are the Best Route 66 Stops in Illinois, Missouri & Oklahoma?
If you’re looking for memorable roadside attractions, these are the places I would recommend adding to your travel plans:
- Pink Elephant Antique Mall, Illinois: Giant roadside attractions, antiques and a retro diner.
- Collinsville, Illinois: The World’s Largest Catsup Bottle and Route 66 murals.
- Granite City, Illinois: Street art, local history and unexpected roadside landmarks.
- Old Chain of Rocks Bridge: Historic Route 66 engineering and Mississippi River views.
- St. Louis, Missouri: Historic Union Station and a worthwhile urban road-trip stop.
- Uranus Fudge Factory, Missouri: Unusual roadside attractions and plenty of humor.
- Springfield, Missouri: Colorful downtown murals and unexpected discoveries.
- POPS 66, Oklahoma: A giant soda bottle, modern architecture and hundreds of colorful sodas.
- Windmill Shops Mural, Oklahoma: A large-scale tribute to Route 66 history.
- Arcadia Round Barn, Oklahoma: Historic architecture and an unforgettable wooden interior.
For me, the appeal of Route 66 isn’t simply checking attractions off a list. It’s taking time to appreciate the places, people and stories that make each community different.
Best Route 66 Stops in Illinois
Illinois was where the Route 66 portion of our Midwest adventure really began to take shape.
Between oversized roadside attractions, historic landmarks and unexpected murals, we found plenty of reasons to slow down.
Pink Elephant Antique Mall
908 Veterans Memorial Drive, Livingston, Illinois 62058
If I had to choose one roadside attraction that captures the wonderfully quirky personality of Route 66, Pink Elephant Antique Mall would be near the top of my list.
Located in a former school building, this destination is much more than an antique store.
Its grounds feature oversized sculptures, colorful roadside figures, a pink elephant and a diner housed inside a giant ice-cream-cone-shaped building.
My brother and I stopped here during our first day on the road. What could have been a quick photo opportunity turned into one of the most memorable experiences of the day.
We enjoyed a hosted lunch and had the opportunity to preview the Haunted School attraction.
It was an unexpected addition to our visit and another reminder that some of the most interesting travel experiences happen when you allow yourself extra time.
Photography tip: Start with wide compositions that show the larger-than-life roadside sculptures in their surroundings. Then move closer to capture individual details. Including a person in the frame can help communicate the enormous scale of some of the attractions.
Before you go: The antique mall currently advertises daily hours of 9 a.m. to 7 p.m. The diner and candy shop have their own schedules, and holiday hours may vary. Check the official Pink Elephant Antique Mall website before visiting.
Read more: Our experience is included in Day 1: Route 66 Roadside Attractions, Murals and Unexpected Adventures →
The World’s Largest Catsup Bottle is a historic water tower and an unforgettable Route 66 roadside landmark in Collinsville, Illinois.
World’s Largest Catsup Bottle
800 South Morrison Avenue, Collinsville, Illinois 62234
Only on Route 66 would a giant catsup bottle become a must-see attraction!
Standing approximately 170 feet tall, the World’s Largest Catsup Bottle is actually a historic water tower.
Built in 1949, it was designed to resemble a bottle of Brooks Old Original Rich & Tangy Catsup.
The tower is one of those wonderfully unusual roadside landmarks that make you appreciate the creativity behind America’s historic highways.
This was a photography stop rather than a ticketed attraction. I enjoyed seeing a familiar everyday object transformed into a towering roadside landmark.
Photography tip: A vertical photograph is especially effective for capturing the tower’s height. Step back far enough to include the supporting steel structure, which helps communicate its enormous scale.
You can learn more about its history through the World’s Largest Catsup Bottle website.
A Route 66 mural in Collinsville, Illinois, celebrating the history of America’s Mother Road.
Collinsville Route 66 Mural
Collinsville also offered another of my favorite road-trip subjects: colorful Route 66 street art.
Murals are something I actively search for when traveling.
They often reveal a community’s identity and provide a different perspective on the places we visit.
Photography tip: Photograph the entire mural before experimenting with closer compositions. I prefer to document the full artwork first, then focus on interesting lettering, illustrations and smaller details.
Granite City — Murals & Roadside Americana
Downtown Granite City, Illinois
Granite City was another destination that surprised me during our road trip.
Located just across the Mississippi River from St. Louis, this community offers an interesting mix of Route 66 history, industrial heritage, colorful murals and unexpected roadside attractions.
Rather than treating Granite City as a quick stop, I recommend allowing time to explore several different locations.
We found plenty of subjects to photograph, including murals, vintage-inspired roadside displays and unusual public art.
One particularly memorable attraction was the Make It Toy monument. It adds another playful dimension to the area’s collection of roadside curiosities.
Granite City also has It’s Electric Neon Sign Park and additional Route 66-inspired murals, making it especially appealing to travelers who enjoy vintage Americana and street photography.
Photography tip: Photograph murals straight on when possible to preserve their proportions. For roadside sculptures, vary your angle and include some of the surrounding environment to tell a more complete story.
For exact locations, more photographs and additional stops, read my complete Granite City guide to murals and Route 66 roadside attractions →
Old Chain of Rocks Bridge connects the history of Route 66 with the landscape of the Mississippi River.
Old Chain of Rocks Bridge
Mississippi River, north of downtown St. Louis
Old Chain of Rocks Bridge offers a completely different Route 66 experience.
Instead of colorful roadside sculptures and murals, this stop celebrates the engineering and transportation history of the Mother Road.
The historic bridge stretches across the Mississippi River and is famous for its distinctive bend.
It once carried Route 66 traffic across the river and is now a destination for walking, cycling and appreciating the surrounding landscape.
We explored the bridge area during our Midwest road trip.
Seeing it in person offered another reminder of the remarkable infrastructure that helped connect communities along Route 66.
Photography tip: The bridge’s steel structure creates strong leading lines. Look for repeating patterns, interesting perspectives and opportunities to include the Mississippi River in the composition.
Important visitor update — October 2026: According to Great Rivers Greenway, the Illinois-side canal bridge is closed for construction from June 22 through the end of 2026. Old Chain of Rocks Bridge remains accessible from the Missouri side only. A separate interstate ramp closure also affects the approach to Chain of Rocks Park.
Before visiting, consult the official Chain of Rocks Park access and detour information.
Best Route 66 Stops in Missouri
Missouri brought another mix of historic architecture, quirky roadside humor and unexpected street art.
Some of our original plans changed along the way, but those spontaneous decisions led to several memorable discoveries.
The historic entrance to St. Louis Union Station, a landmark destination in downtown St. Louis, Missouri.
St. Louis Union Station
1820 Market Street, St. Louis, Missouri 63103
St. Louis is a natural destination to include when exploring Route 66 through Missouri, even if you choose to spend time at attractions beyond the original highway alignment.
During our visit, we explored the St. Louis area and included Union Station among our stops.
This historic transportation landmark offers beautiful architecture and an interesting connection to the city’s travel heritage.
I always enjoy photographing historic architecture, and Union Station offers plenty of interesting details.
Its substantial stonework, decorative features and railroad history make it an appealing stop for travelers interested in more than roadside attractions.
Photography tip: Look for symmetry, repeating architectural elements and decorative details. Photographing entrances and signage can also help preserve a sense of place.
Union Station was part of our broader St. Louis experience rather than a preserved roadside Route 66 attraction. That distinction is worth keeping in mind when planning your own trip.
For more about our first travel day, read our Route 66 journey into St. Louis →
A playful roadside rocket at Uranus Fudge Factory, one of our unexpected Missouri road-trip stops.
Uranus Fudge Factory
Historic Route 66 corridor near St. Robert, Missouri
Some roadside attractions are subtle.
Uranus Fudge Factory is definitely not one of them!
Between the humorous billboards, colorful storefronts and oversized roadside displays, this destination is designed to make passing travelers curious enough to stop.
We hadn’t originally planned to spend time here, but after seeing the roadside advertising, we decided to investigate.
The attraction leans heavily into silly, sometimes cheeky humor.
It’s not necessarily everyone’s style, but the colorful roadside setting certainly makes it memorable.
For me, the best part was discovering another unexpected photography subject that hadn’t been included in our original itinerary.
Photography tip: Use wide compositions that capture the colorful roadside displays and the attraction’s larger-than-life personality. Details in the signs and storefronts can also make fun supporting photographs.
Travel note: Because the attraction relies on suggestive wordplay, families may want to preview it before stopping with younger children.
Read more about our unexpected Missouri stops in Road Trip Day 3: Why the Best Stops Were Never Part of the Plan →
A Ferris Bueller-inspired Ferrari mural was one of my favorite photography discoveries in Springfield, Missouri.
Downtown Springfield Route 66 Murals
Downtown Springfield, Missouri
Springfield is closely connected with Route 66 history, but our visit didn’t unfold exactly as planned.
We had originally considered visiting the Route 66 Car Museum.
Instead, we changed our plans and spent time photographing murals around downtown Springfield.
We discovered seven murals, and one of my favorites featured a Ferrari inspired by the movie Ferris Bueller’s Day Off.
This stop reminded me why I love incorporating street art into my travel experiences.
Murals can turn an ordinary downtown walk into a colorful adventure, and they often reveal unexpected connections to popular culture and local history.
Photography tip: Photograph the entire mural before experimenting with close-ups. Try different angles to avoid reflections, parked vehicles and distracting background elements while keeping the artwork accurately represented.
What about the Route 66 Car Museum? Although it was on our original list, we did not visit. It remains a possibility for a future trip. Travelers interested in classic automobiles can find current information on the Route 66 Car Museum website.
Joplin and several other Missouri Route 66 attractions also remain on my list for another journey.
Rather than recommend places I haven’t experienced, I prefer to keep this roundup focused on the stops we actually made.
Best Route 66 Stops in Oklahoma
Oklahoma offered some of the most visually interesting Route 66 attractions of our trip.
In particular, the small community of Arcadia combines unusual modern architecture, colorful street art and a remarkable historic building.
If you’re traveling through the Oklahoma City area, I recommend setting aside time for these three stops.
POPS 66 Soda Ranch
660 West Highway 66, Arcadia, Oklahoma 73007
You certainly won’t mistake POPS 66 for an ordinary convenience store.
Located along historic Route 66, this modern roadside attraction features a towering 66-foot soda bottle outside its entrance and an extraordinary assortment of colorful bottled drinks inside.
From a photography standpoint, POPS is a wonderful stop.
The bottle creates a dramatic outdoor focal point, while the interior offers colorful repeating patterns and vibrant displays.
Our restaurant experience was less impressive than the photography opportunities.
We found the burger, fries and shake fairly average for the price, and lunch took more than an hour.
Would I stop again? Absolutely, but primarily for the architecture, colorful soda displays and photography.
If I were working with a tight driving schedule, I wouldn’t make a restaurant meal the main reason for visiting.
Photography tip: Photograph the exterior bottle vertically to emphasize its height. Inside, look for symmetry and color patterns in the soda displays. A return visit around dusk could offer an opportunity to photograph the illuminated bottle.
Before you go: POPS currently lists store hours of 6 a.m. to 10 p.m. and restaurant hours of 10:30 a.m. to 9 p.m., with separate weekend breakfast hours. Verify details on the official POPS website.
For more details about this stop and the nearby attractions, read my Route 66 in Arcadia, Oklahoma travel guide →
The Windmill Shops Centennial mural tells the story of Arcadia and Route 66 through colorful historic imagery.
Windmill Shops Route 66 Centennial Mural
Windmill Shops, near North Odor Street, Arcadia, Oklahoma
Just a short distance from POPS, the Windmill Shops mural offers a completely different look at Route 66.
Stretching approximately 225 feet along the back of the Windmill Shops building, this colorful mural celebrates Arcadia’s history and its connections to America’s Mother Road.
What makes this mural particularly interesting is its storytelling.
Rather than presenting a single image, the artwork combines scenes from local history with iconic Route 66 imagery.
It’s also easy to overlook if you don’t know where to look, since the mural is located on the back of the building rather than facing the main highway.
Photography tip: With a mural this large, one photograph rarely does the entire artwork justice. Capture a wide establishing image, then photograph individual scenes and details that help tell the story.
For additional details and photography suggestions, read my Windmill Shops Route 66 Centennial Mural feature →
Arcadia Round Barn
107 East Highway 66, Arcadia, Oklahoma 73007
Of all the historic buildings we visited along this portion of Route 66, the Arcadia Round Barn was one of the most fascinating from an architectural perspective.
Built in 1898, the barn predates the original Route 66 highway.
Its circular design makes it immediately recognizable from the road, but the interior is what really captured my attention.
Inside, the upper loft reveals an extraordinary arrangement of curved wooden rafters.
Their repeating lines create a striking architectural composition, and it’s easy to spend more time than expected looking upward.
For me, the barn was a welcome contrast to the modern roadside architecture of POPS.
Both attractions are memorable, but in completely different ways.
Photography tip: Capture the circular exterior from a position that reveals its unusual shape. Inside the loft, experiment with symmetrical compositions that emphasize the repeating wooden beams.
Accessibility note: The upper loft requires stairs, so visitors with mobility concerns should verify available access before arriving.
Before you go: The Arcadia Historical and Preservation Society lists free admission, with donations welcomed. Posted hours are generally 10 a.m. to 5 p.m., but seasonal notices, volunteer availability and severe weather may affect opening times. Check the official Arcadia Round Barn visitor information.
For a closer look at all three Arcadia attractions, visit my complete Arcadia Route 66 guide →
Photography Tips for a Route 66 Road Trip
One of my favorite things about Route 66 is the variety of photography opportunities.
You can photograph a giant roadside sculpture in the morning, historic architecture in the afternoon and a colorful mural before reaching your hotel.
Here are a few practices that worked well during our Midwest adventure.
If you enjoy photographing destinations as much as I do, explore my Street Art Maps & Photo Spots → for additional inspiration.
How to Plan a Route 66 Road Trip Through These Three States
Although these attractions are spread across Illinois, Missouri and Oklahoma, you don’t have to drive the entire length of Route 66 to enjoy them.
Instead of trying to squeeze every attraction into one rushed itinerary, consider organizing your stops by region.
Illinois: Focus on the St. Louis Region
Livingston, Collinsville, Granite City and Old Chain of Rocks Bridge make a rewarding collection of historic Route 66 stops. You can combine roadside attractions, public art and history without constantly switching between unrelated activities.
Missouri: Make Time for Unexpected Discoveries
St. Louis offers plenty of attractions worth exploring, while the historic Route 66 corridor farther west features quirky roadside destinations and communities with their own stories.
Springfield is particularly appealing if you enjoy murals and local history.
Oklahoma: Explore Arcadia Near Oklahoma City
Arcadia is one of the easiest places to enjoy several very different Route 66 attractions within a relatively small area.
POPS 66, the Windmill Shops mural and Arcadia Round Barn can be explored in approximately two hours if you skip a lengthy meal. Allow closer to three hours if you prefer a more relaxed pace.
For the detailed route we actually traveled, including our other Midwest destinations, accommodations and day-by-day experiences, see my 8-Day Midwest Road Trip Itinerary →
Frequently Asked Questions About Route 66 Stops
What are the best Route 66 roadside attractions in Illinois?
Based on my firsthand travels, some of my favorites include Pink Elephant Antique Mall in Livingston, the World’s Largest Catsup Bottle in Collinsville, Granite City’s murals and roadside attractions and Old Chain of Rocks Bridge near St. Louis.
Is Route 66 worth visiting if you aren’t driving the entire highway?
Absolutely. Many Route 66 attractions work beautifully as individual stops or regional road trips. You can experience roadside Americana, historic sites, interesting communities and local attractions without driving from Chicago to California.
Is POPS 66 in Oklahoma worth visiting?
Yes, especially if you enjoy unusual architecture, colorful displays and roadside photography. Based on my experience, the main attractions are the giant soda bottle and the enormous selection of bottled drinks rather than the restaurant meal.
Can you visit POPS 66 and Arcadia Round Barn on the same day?
Yes. POPS 66, Arcadia Round Barn and the Windmill Shops mural are close enough to enjoy during the same outing. I recommend allowing approximately two to three hours to explore and photograph all three without rushing.
Is Old Chain of Rocks Bridge open in 2026?
As of October 2026, the historic bridge remains accessible from the Missouri side. The Illinois-side canal bridge is closed for construction through the end of 2026. Always check Great Rivers Greenway’s current park alerts before visiting.
What should photographers look for along Route 66?
Look for historic signs, oversized roadside sculptures, vintage buildings, murals, bridges, diners, unusual architecture and details that reflect local culture. Some of the best photo opportunities are found in smaller communities rather than at the most famous attractions.
Why I Love Exploring Route 66
After traveling through portions of Route 66 in Illinois, Missouri and Oklahoma, I came away with a greater appreciation for the places that give the Mother Road its personality.
Some destinations impressed me with their architecture. Others made me laugh. A few simply gave me another wonderful excuse to stop, pull out my camera and explore somewhere new.
That’s what I enjoy most about a road trip. The destination matters, but so do the unexpected discoveries along the way.
Whether you’re planning a long-distance Route 66 adventure or a weekend getaway focused on a handful of interesting stops, I hope these firsthand recommendations inspire you to see more of the communities and roadside landmarks that make this historic highway special.
Have you traveled Route 66? Which roadside attraction or small-town discovery was your favorite? I’d love to hear about it in the comments!
See the World. Frame the Adventure.
About Angela
Angela Addington is the travel photographer and writer behind Lenses & Latitudes. She shares firsthand destination guidance and practical photography advice for independent and solo travelers, women over 50, road-trippers and weekend explorers. Learn more about Angela.
