A Four-Day Route 66 Road Trip
Let's take a trip through The Mother Road from Chicago to its semi-official Capital, Tulsa.
Downtown Tulsa | Mick Haupt via Unsplash
More than 2,400 miles—sometimes called the Main Street of America. It dips and curves across the landscape, neon-lit and dotted with roadside attractions and natural wonders that awe. Excerpted from our Route 66 field guide, here is a four-day trip down The Mother Road, taking you from Chicago to the Route's unofficial capital, Tulsa.
CHICAGO TO SPRINGFIELD, IL
The journey begins across from The Art Institute of Chicago.
In the heart of downtown Chicago a small sign above a “Historic Route 66” marker reads “BEGIN.” The first pit stop comes quick. LOU MITCHELL'S doles out banana pancakes and jumbo omelets—also known for “Serving the world’s finest COFFEE” since 1923. The metropolis gradually gives way to sleepier suburbs and farmland. Stop for a stretch at OLD JOLIET PRISON, made famous in The Blues Brothers. Small towns dot the roadside, each with its own character. AMBLER'S TEXACO STATION in Dwight and the Standard Oil Station in Odell, are each restored and listed on the National Register of Historic Places. Pontiac’s Route 66 Museum includes artist Bob Waldmire’s Volkswagen Microbus. Have a chat with Terri Ryburn at the Sprague Super Station in Normal, an example of 1930s roadside architecture. When you reach Springfield, capital city and, crucially, home of the corndog, dinner-on-a-stick awaits at COZY DOG DRIVE IN.
SPRINGFIELD, IL TO CUBA, MO
From the Land of Lincoln to Mark Twain National Forest.
The Route 66 Experience, at the Illinois State Fairgrounds in Springfield, makes for a delightfully over-the-top immersion into 66-iana—neon and vintage billboards capturing the great road’s razzle-dazzle. Beyond, a stop in Litchfield is rewarded with another Mother Road classic–steaks, pork chops, Greek-style chicken livers at century-old ARISTON CAFE. A couple of towns farther on, Livingston’s Pink Elephant Antique Mall is notable for ... yes, its giant pink elephant, as well as other super-sized fiberglass figures. In contrast to all this small-town Americana, St. Louis could warrant a full big-city exploration. Make time for the iconic Chain of Rocks Bridge on the Missouri border and brake for frozen custard at TED DREWES. The dramatic Stage Curtain at Meramec Caverns, near Stanton, has been drawing audiences to its lacy macramé of limestone deposits since 1935. Neon old and new lights the way to WAGON WHEEL MOTEL, the oldest continuously operated motel on Route 66 still cozy in its stone-walled mini-cabins.
Route 66
Field Guide
Get the full 14-day road trip story in our Route 66 Field Guide full of roadside attractions, pie pit stops, motor lodges and more.
CUBA TO CARTHAGE, MO
Route 66 through Missouri was fully paved by 1931, just five years after the adventure began.
West of Newburg take the Hooker Cut section of Route 66, site of a ghost town-esque vestige of roadside life where highway lanes cut into natural stone. This leads to Devil’s Elbow, where a historic truss bridge crosses the Big Piney River and looks out on Uranus, Missouri, full of kitsch. You’re in Ozark country now. St. James has wineries to explore. MUNGER MOSS MOTEL in Lebanon has a world-famous neon sign. Downtown Springfield’s History Museum on the Square explores the city’s claim to fame as the Birthplace of Route 66, where, in 1926, officials selected the number 66, thus giving form to an American legend in the making. In Paris Junction, stop for a chat and a slice of watermelon with George Bowick and Barbara Barnes as they carry on the legacy of GARY'S GAY PARITA, a replica rebuild of a twice-incinerated 1930s Sinclair service station, undertaken by Barbara’s father, the eponymous Gary. Rest up in Carthage at Boots Court Motel, a vision of Streamline Moderne architecture.
CARTHAGE TO TULSA
One day. Three states. Missouri, Kansas and Oklahoma
Once you cruise through Joplin, you’re on Kansas’ doorstep, with just 13.2 miles of Route 66 cutting across the state’s southeast corner. Just over the state line in Galena, Aaron Perry is the consummate host at GEARHEAD CURIOS. Generous with conversation and route intel as he presides over a former Texaco station turned gift shop. From here, it’s just about 10 miles to route’s end in Kansas, and then ...Oklahoma! The first major town this side of the border is Quapaw (population 806), which once bustled as part of a tristate mining district. Stop at the fire station to sign the giant rock–with much still to see ahead.
COLEMAN THEATRE Miami
Built in 1929 in Spanish Colonial Revival style for mining magnate George Coleman, showcases demonstrations of its original pipe organ.
SIDEWALK HIGHWAY Narcissa
One of the most distinctive stretches on 66–only 9 feet wide!
HI-WAY CAFE Vinita
Classic giant figures guard a down-home feast (omelets, chicken-fried steak, patty melts).
WILL ROGERS’ MEMORIAL MUSEUM Claremore
Pay respects to multihyphenate entertainer: vaudevillian, humorist, actor, cowboy- philosopher. The Cherokee Nation oversees its famed citizen’s gravesite.
THE BLUE WHALE Catoosa
Brainchild of zoologist Hugh S. Davis, this 80-foot marine mammal built in 1972 welcomes visitors to walk out over a pond through its smiling open mouth.
Once in Tulsa, you’ve reached the (semi-official) Capital of Route 66, home to oilman and former state highway commissioner Cyrus Avery, a.k.a. the “Father of Route 66.” A small blue neon sign lights the way for The Campbell Hotel, a route-side stay in the heart of the Mother Road.
