Cynics don't last on Route 66. Some may start the drive in Chicago skeptical of travelers who gush about this time capsule of a highway hiding cheerful truck-stop waitresses, kids playing on tire swings and restaurant owners personally serving up plates of comfort food.
But it doesn't take long to see that warm-hearted cliches stubbornly survive on the Mother Road. And when contemporary stresses leave you longing for a shot of American idealism, Route 66 delivers.
It's only natural to start in the Midwest when following Route 66's 2,448 miles across eight states. The road, which had an official life from 1926 to 1985, began in Chicago and, like the country's dreams, headed west all the way to the Pacific, ending in Santa Monica. The Midwestern portion takes you as far as Tulsa.
The route rarely strays far from the interstate, making it easy to jump on and drive a section as time allows. But before you set out, buy a good set of maps or a guidebook. Route 66 signs are maddeningly spotty in some states.
And be sure to retain a healthy taste for discovery. Nobody drives the Mother Road so they can patronize franchises. The following slides contain dozens of our unique finds along the tour.
Route 66's start, Chicago: Purists begin their drive at the Mother Road's original starting point: the corner of Jackson and Michigan at Grant Park.
Lou Mitchell's, Chicago: Day One's traditional breakfast occurs on a red vinyl seat at this landmark (left) that opened on Jackson Boulevard three years before Route 66. Lou's gets the little touches right: free doughnut holes for everyone and a special box of Milk Duds just for ladies. loumitchellsrestaurant.com 
Route 66 Experience: Joliet, Illinois Outside town, cruise by the prison where Jake and Elwood did time in The Blues Brothers. At the new Joliet Area Historical Museum's Route 66 Experience, preview your trip with a mural and film, then grab a turn-by-turn driving guide in the gift shop.
Gemini Giant: Wilmington, Illinois The kitsch caravan begins in earnest at the Launching Pad Drive-In's 27-foot-tall spaceman (left). Born in the '60s with a muffler in hand, the giant picked up a space helmet and rocket over the years.
Gemini Giant 
Standard Oil Station, Odell, Illinois: This quiet town's restored 1932 station (left) is a Route 66 jewel filled with roadside memorabilia such as oil cans and pop bottles. If no one's around to give a tour, press the blue button for a recorded narrative about the station.
Route 66 Hall of Fame & Museum, Pontiac, Illinois: Museums like this one in an old firehouse are the watercoolers of the road, the place to meet fellow travelers and pick up tips on what to see. Hang out here, and you'll quickly find a place in the road's community.
Standard Oil Station 
Memory Lane, Lexington, Illinois: An old route segment is now open only to pedestrians who stroll the asphalt, checking out retro billboards and listening to the hum of passing cars.
Burma-Shave Signs, Towanda, Illinois: Another closed stretch of road features the famous rhyming roadside ads ("A beard that's rough and overgrown is better than a chaperone").
Funks Grove Maple Sirup, Funks Grove: Since 1891, the same family has tapped the same maple grove. The spelling? A family matriarch insisted the word was originally "sirup," and demanded it stay that way. While here, cross 66 and follow a gravel road through the maples to the Funk family's tranquil cemetery and chapel.
Memory Lane 
Abraham Lincoln Sites, Springfield, Illinois: Lincoln built his career here, left for the White House from here and is buried here. It's worth delaying your drive to see the Old State Capitol where he worked, the outstanding presidential museum, his law office and his awe-inspiring tomb at Oak Ridge Cemetery.
Lincoln's tomb 
Cozy Dog Drive In, Springfield, Illinois: Ed Waldmire Jr. created his "crusty cur" during World War II, then gave it a more marketable name when he came home to Springfield. (You'd know it as a corn dog.) Work through a sack of dogs as you wander the 66 memorabilia collection.
Cozy Dog Drive In 
Ariston Cafe, Litchfield, Illinois: Here's the reprieve from fried-food burnout. The storied 1935 cafe (a member of the Route 66 Hall of Fame) features white linen tablecloths and entrees such as grilled swordfish. Ask owner Nick Adam to let you browse his collection of 66 books autographed by drivers from Japan and Germany.
Henry's Rabbit Ranch, Staunton, Illinois: An insurance agent in his day job, Rich Henry leaped into Route 66 culture by building a throwback stop from scratch. Pet the live bunnies, wander a yard full of museum-quality neon motel signs and strike a pose sitting atop the giant rabbit (left).
Henry's Rabbit Ranch 
Ariston Cafe 
Chain of Rocks Bridge, Granite City, Illinois: The route once crossed this famed steel bridge that stretches a mile across the Mississippi between Illinois and Missouri, including a distinctive dogleg turn in the middle of the river. The renovated bridge now serves pedestrians and bikers. On the horizon, the Gateway Arch glitters in the sun.
Ted Drewes Frozen Custard, St. Louis, Missouri: For the full experience, flip your cup upside down for a couple of seconds. Ted's famed custard, thicker than even St. Louis' summer air, won't fall out. teddrewes.com 
Route 66 State Park, Eureka, Missouri: Stop in for one of the all-time oddest state park stories. Soil pollution caused the government to incinerate the entire Times Beach housing development in the 1980s, leaving a park full of quiet trails. Learn the story via exhibits in what was once Steiny's swingin' roadhouse. mostateparks.com/route66.htm 
Meramec Caverns, Stanton, Missouri: Meramec was a longtime must-see on All-American road trips, and pop culture still lurks everywhere on the cave tour. Jesse James hid out along the underground river. A side room hosted honeymooners for 10 days in a 1950s' TV stunt, and an episode of Lassie--the one where Lassie rescues Timmy--was filmed inside.
Missouri Hick BBQ, Cuba, Missouri: The name's enough to make you pull over, but the smoked meats and eye-catching building (featuring a water mill and boards cut at the lumber mill next door) justify the stop.
Meramec Caverns 
Missouri Hick BBQ 
World's Largest Rocking Chair, Fanning, Missouri: New to the "world's largest" category: a 42-foot-high rocking chair erected in 2008 outside a general store (and archery range).
Stonehenge, Rolla, Missouri: Engineering students at the Missouri University of Science and Technology set up a half-size granite version of the legendary stones. As a working sun-based clock, it's reportedly accurate to within 15 seconds.
Missouri Stonehenge 
John's Modern Cabins, Doolittle, Missouri: Follow an abandoned access road to old log buildings (left) that once hosted travelers. The neon sign hasn't glowed in years but still stands tall in the shadows.
Devils Elbow: The devilishly named stretch of blacktop winds through hills, riverbeds and forests. Stop in to chat with the locals on the porch of the post office/general store for the town of Devils Elbow.
John's Modern Cabins 
Munger Moss Motel, Lebanon, Missouri: You don't stay here for wireless Internet access or even an iron in your room. The Munger Moss (complete with vintage neon sign) is a perfectly preserved (and clean) road motel from decades past. Splurge on the $2 upgrade for a king-size bed; it's still only $49.
Munger Moss Motel 
Route 66 Museum, Lebanon, Missouri: Exhibits in the town library feature re-created scenes from a diner and one of the road's most infamous no-tell motels: St. Louis' Coral Court.
Bell Restaurant, Lebanon: Five bucks here buys more country-style breakfast than you can eat. The waitresses may smoke at the counter, but they'll never let your coffee get cold.
State Line: Borders don't get much simpler: A white stripe painted across the asphalt outside a bar marks the passage from Missouri to Kansas.
4 Women on the Route, Galena, Kansas: Several gal pals recently restored an old gas station, adding a gift shop and small cafe. The real star is a rusty truck (left) that inspired Pixar animators as they drove Route 66 researching the movie Cars several years ago. Melba Rigg ("Like the toast," she says) can't wait to snap your photo with the original Tow-Mater. Even if you don't have kids along, this stop's a delight.
4 Women on the Route 
Eisler Brothers Store, Riverton, Kansas: Buy a sandwich at the deli counter in the old general store, and pull up a chair on the front porch a few yards from the road. Finish up with a Route 66 Root Beer out of the vintage soda cooler (with built-in bottle opener).
Mickey Mantle's boyhood home, Commerce, Oklahoma: The house at 319 S. Quincy represents a genuine sports pilgrimage. Legend says the corrugated shed got its dents when the Mick hit pitches thrown by his dad after long days in the local mines.
Clanton's Cafe, Vinita, Oklahoma: This 1927 landmark's neon sign (left) says it all: "Eat." The chicken-fried steaks draw TV crews and magazine writers, but it's worth stopping for cream pie and coffee even if you pass through Vinita between meals.
Clanton's Cafe 
Andy Payne Statue, Foyil, Oklahoma: A roadside monument honors a local teen who won the "Bunion Derby" cross-country foot race in 1928. After averaging roughly 40 miles a day for more than 80 days, Payne said, "I just thought I could do it."
Giant Totem Pole, Foyil: For the definition of "eccentric folk art," detour a few miles off Route 66 and gaze up at the funky paintings of Native Americans and animals on the 90-foot concrete totem pole (left) Ed Galloway built in his retirement.
Giant Totem Pole 
Andy Payne Statue 
Will Rogers Memorial, Claremore, Oklahoma: No American has ever surpassed the star power Will Rogers attained in the 1920s and 1930s. A massive, Spanish-style museum reminiscent of presidential libraries honors the beloved actor/writer/philosopher who said, "I've never met a man I didn't like." A statue of Will on horseback guards the family grave and overlooks Claremore in the Tiawah Valley.
Will Rogers Memorial 
Blue Whale, Catoosa, Oklahoma: The swimming hole leviathan had slipped into disrepair a few years ago. But locals saved the whale, ensuring photo ops for another generation.
(A version of this story appeared in Midwest Living® March/April 2009. It was updated in 2012. Prices and other details can change; please check specifics before you make travel plans.)
Blue Whale