Looking for an easy getaway that’s packed with fun? Load up the car and head for Route 66! In Illinois, the last 100 miles of this iconic highway travels through the southwest part of the state just outside St. Louis, before crossing the Mississippi River into Missouri. It’s the only place in America where the Mother Road meets the Great River Road, winding along three of our country’s great rivers in a trip that’s full of historical landmarks, quirky Americana, and small-town charm.
“Route 66 isn’t just a highway,” says Casey Claypool, local business owner and Executive Director of Illinois Route 66 Scenic Byway. “It’s a heartbeat, a thread that stitches together small towns, big dreams, and stories you won’t find in any guidebook.” Whether you’re a road trip veteran or an excited newcomer, there’s never been a better time to explore everything this unforgettable stretch of highway has to offer.
The Last 100 Miles of Route 66 in Illinois Offers the Ultimate Road Trip Adventure
For history buffs, the Litchfield Museum and Route 66 Welcome Center is a must. This retro-designed building, housed on the site of a former gas station, offers a window into the past with local artifacts and memorabilia from Litchfield's heyday as a popular rest stop for Mother Road travelers. There are also two beautifully preserved service stations, the West End Service Station in Edwardsville and the Soulsby Service Station in Mt. Olive, where you can step back in time and imagine Route 66 in all its midcentury glory.
For more local history, Carlinville boasts two structures with fascinating backstories. The Macoupin County Cannonball Jail employed a unique "cannonball method" where hollowed-out stones were filled with leftover Civil War cannonballs. Nearby stands the infamous "Million Dollar Courthouse," designed by the same architect. This extravagant building represents perhaps the most egregious case of government overspending in Illinois history, and today visitors can tour the courthouse and jail for a trip back in time.
Step Into the Stories of Route 66 and
Small-Town Legends
The heart of the journey lies in the small towns and the diners where locals know your name and the unexpected conversations that make the miles meaningful.”
"
“What I love most about traveling Route 66,” says Claypool, “Is discovering the small businesses that still carry the spirit of the road - places where history, community, and a sense of belonging come alive.” For roadside Americana at its finest, check out the Pink Elephant Antique Mall in Livingston. This eclectic shopping destination features vintage goodies from over 50 dealers, as well as a menagerie of oversized statues outside.
Another essential stop is the Brooks Catsup Bottle Water Tower in Collinsville. This beautifully restored tower stands tall at 170 feet and is a popular photo stop for travelers year-round. And night owls shouldn't miss the It's Electric Neon Sign Park in Granite City, where meticulously restored neon signs from the city's past glow brilliantly from dusk until dawn.
Quirky Icons & Timeless Charm:
Where the Spirit of Route 66 Lives On
Learn More
By Monica Vanover on May 23, 2025
West End Service Station where travelers and locals frequented the station to re-fuel, get an oil change, check their tires, and enjoy a cold soda.
- Casey Claypool, Executive Director of Illinois Route 66 Scenic Byway
Insert your client's headline here to engage potential clients
Pose for pictures with the oversized outdoor statues including the pink elephant, authentic "muffler man" and more!
The World's Largest Catsup Bottle rises high above Collinsville, IL just off Route 159.
Families traveling the route will find plenty of fascinating stops to engage visitors of all ages. Cahokia Mounds in Collinsville is a UNESCO World Heritage Site featuring the remains of America's most sophisticated prehistoric civilization; on a clear day, you can see downtown St. Louis from the top of Monks Mound. Another popular spot is the iconic Chain of Rocks Bridge just north of St. Louis, which spans 5300 feet across the Mississippi River and has a unique 30-degree bend that makes it the perfect place for peaceful overlooks and epic photographs.
In Glen Carbon, the restored Yanda Log Cabin provides insight into a simpler time through events like apple butter festivals and pioneer days. Young travelers will also enjoy the interactive exhibits at the Edwardsville Children's Museum, while bookworms can browse the selection at the Sly Fox
Bookstore in Virden, which specializes in children's books, American history, and Route 66 literature.
When it comes to entertainment, Route 66 delivers. The Wildey Theatre in Edwardsville has over 75 years of history hosting everything from opera to vaudeville shows, and continues its tradition today as a beloved cultural hub. For a true slice of Americana, don’t miss the Skyview Drive-In in Litchfield, which is the last remaining drive-in on Route 66 in Illinois and offers an authentic cinematic experience under the stars.
But, as Claypool explains, activities and attractions are only half the fun when it comes to traveling Route 66. “Newbies might be surprised to discover that Route 66 isn’t just about vintage cars and neon signs; it’s about the people,” she says. “The heart of the journey lies in the small towns, the mom-and-pop shops, the diners where locals know your name after one visit, and the unexpected conversations that make the miles meaningful.”
More Than a Road Trip: Entertainment, Nostalgia, and the People Who Make It Special
For a taste of local nightlife, Decamp Station in Staunton offers hearty food, live music, and outdoor recreation including sand volleyball and baseball. Weezy's Bar & Grill in Hamel serves classic American fare in a charming spot decked out with vintage signs. Enjoy the authentic pub vibes at the Stagger Inn Again in Edwardsville, the area’s oldest drinking establishment that never closed its doors on the good times. History and libations combine at the Luna Café in Mitchell, a favorite hideout of mobster Al Capone during Prohibition that now serves steak and seafood along with plenty of Route 66 memorabilia.
As historic Route 66 heads into its hundredth year, don’t miss the special celebrations that mark this exciting milestone. Travel the Route 66 Postcard Mural Trail to discover 11 hand-painted murals that celebrate this iconic road, as well as the charming southwest Illinois towns that make it so special. Also, make sure to check out the Route 66 Monument Trail, where you’ll find eight whimsically oversized Route 66 shields that make for first-rate photo opportunities.
Be a part of the Route 66 renaissance by traveling the Route 66 Monument Trail, a set of eight larger than life Route 66 shields.
So what are you waiting for? The final stretch Route 66 in southwest Illinois is an absolute must for a unique trip you’ll never forget. Claypool agrees, calling this magical stretch of highway “A living, breathing piece of history that still evolves - quirky, authentic, and deeply personal.” Visit their website today and get ready for a journey where classic road trip nostalgia meets the majesty of America's great rivers.
Claypool’s spot, Doc's Just Off 66, has been a cornerstone of Girard since 1884, evolving from a pharmacy and general store to a restaurant serving American diner classics and Route 66 memorabilia. The longest-operating restaurant along the entire Route 66 the Ariston Café in Litchfield is a local favorite with a menu full of Southern, Italian, and Greek cuisine.
Dessert lovers will find plenty to cheer about on their trip. Jubelt's Bakery & Café in Litchfield is a century-old family business in the Route 66 Hall of Fame that serves up fresh baked goods and a full menu every day. The Route 66 Creamery in Hamel dishes out old-fashioned ice cream and hand-pressed steak burgers on a dog-friendly covered patio complete with hanging swings. In nearby Collinsville – known as the International Horseradish Capital of the World – Old Herald Brewery & Distillery offers house-crafted beers, spirits, and a menu that nods to the region’s spicy claim to fame. They even produce a horseradish vodka made with locally sourced horseradish – amazing in a Bloody Mary, and adding a flavorful detour for curious travelers.
Sponsored by Great Rivers & Routes
Route 66 isn’t just a highway. It’s a heartbeat, a thread that stitches together small towns, big dreams, and stories you won’t find in any guidebook."
"
- Casey Claypool, Executive Director of Illinois Route 66 Scenic Byway
Be a part of the Route 66 renaissance by travelling the Route 66 Mural Trail, a collection of 11 Americana-themed murals.
Learn More
The bridge gets its name from a natural feature of the Mississippi just south of the bridge- a chain of rocks that drops several feet in a shallow area of the river and creates a series of rapids.
Looking for an easy getaway that’s packed with fun? Load up the car and head for Route 66! In Illinois, the last 100 miles of this iconic highway travels through the southwest part of the state just outside St. Louis, before crossing the Mississippi River into Missouri. It’s the only place in America where the Mother Road meets the Great River Road, winding along three of our country’s great rivers in a trip that’s full of historical landmarks, quirky Americana, and small-town charm.
“Route 66 isn’t just a highway,” says Casey Claypool, local business owner and Executive Director of Illinois Route 66 Scenic Byway. “It’s a heartbeat, a thread that stitches together small towns, big dreams, and stories you won’t find in any guidebook.” Whether you’re a road trip veteran or an excited newcomer, there’s never been a better time to explore everything this unforgettable stretch of highway has to offer.
Step Into the Stories of Route 66 and
Small-Town Legends
For history buffs, the Litchfield Museum and Route 66 Welcome Center is a must. This retro-designed building, housed on the site of a former gas station, offers a window into the past with local artifacts and memorabilia from Litchfield's heyday as a popular rest stop for Mother Road travelers. There are also two beautifully preserved service stations, the West End Service Station in Edwardsville and the Soulsby Service Station in Mt. Olive, where you can step back in time and imagine Route 66 in all its midcentury glory.
For more local history, Carlinville boasts two structures with fascinating backstories. The Macoupin County Cannonball Jail employed a unique "cannonball method" where hollowed-out stones were filled with leftover Civil War cannonballs. Nearby stands the infamous "Million Dollar Courthouse," designed by the same architect. This extravagant building represents perhaps the most egregious case of government overspending in Illinois history, and today visitors can tour the courthouse and jail for a trip back in time.
“What I love most about traveling Route 66,” says Claypool, “Is discovering the small businesses that still carry the spirit of the road - places where history, community, and a sense of belonging come alive.” For roadside Americana at its finest, check out the Pink Elephant Antique Mall in Livingston. This eclectic shopping destination features vintage goodies from over 50 dealers, as well as a menagerie of oversized statues outside.
Another essential stop is the Brooks Catsup Bottle Water Tower in Collinsville. This beautifully restored tower stands tall at 170 feet and is a popular photo stop for travelers year-round. And night owls shouldn't miss the It's Electric Neon Sign Park in Granite City, where meticulously restored neon signs from the city's past glow brilliantly from dusk until dawn.
Quirky Icons & Timeless Charm:
Where the Spirit of Route 66 Lives On
- Casey Claypool, Executive Director of Illinois Route 66 Scenic Byway
West End Service Station where travelers and locals frequented the station to re-fuel, get an oil change, check their tires, and enjoy a cold soda.
The heart of the journey lies in the small towns and the diners where locals know your name and the unexpected conversations that make the miles meaningful.”