There are as many ideas about must-see attractions as there are roadies, but here are some of my favorites. (Being a total piglet, I have a LOT of restaurants on my list. Bring your appetite; road food is a beautiful thing.)
McCook, IL: Snuffy's diner. This place epitomizes Chicago.
Joliet, IL: Joliet Area Historical Museum and Route 66 Welcome Center.
Wilmington, IL: Gemini Giant.
Gardner, IL: Riviera restaurant, old speakeasy, and restored trolley car diner out back.
Odell, IL: Standard Oil Station.
Funks Grove, IL: Home of Funks Grove Maple Sirup (spelled with an "i" instead of a "y" because it contains no added sugar). Get a jug of sirup to take home, but more importantly, get some candy. The regular maple candy is wonderful, but you will absolutely feel like you need a cigarette after you take a bite of one of their maple truffles. Hopelessly decadent.
Atlanta, IL: There's a little grocery store just off 66 where you can get a big styrofoam cup full of deep-fried chicken gizzards or livers suitable for consuming with beer at the tavern on the corner.
Lincoln, IL: Ghost bridge.
Springfield, IL: Home of Abe Lincoln, Bill Shea's petroliana and Route 66 museum, and the birthplace of the corn dog -- the Cozy Dog Diner.
Raymond, IL: Our Lady of the Highways shrine.
Mt. Olive, IL: Soulsby Station.
Staunton, IL: Henry's Route 66 Rabbit Ranch (Hare it is!); Country Classic Cars.
Hamel, IL: Meramec Caverns barn, neon cross.
Mitchell, IL: Luna Cafe. Great old roadhouse.
Madison, IL: Old Chain of Rocks Bridge.
Collinsville, IL: Cahokia Mounds.
Fairmont City, IL: Taqueria El Gallo Jiro. Best tacos on the road. Try the barbacoa.
St. Louis, MO: Ted Drewes' Frozen Custard; off the road is the Museum of Transportation, home to the late, great Coral Court Motel.
Times Beach, MO: Route 66 State Park.
Stanton, MO: Meramec Caverns.
Union, MO: Indian Harvest.
Cuba, MO: Murals. Lots and lots of murals. And the Wagon Wheel Motel. And Missouri Hick barbecue, which is awesome.
Rolla, MO: Mule Trading Post; Rolla Motors.
Newburg, MO: John's Modern Cabins.
Devil's Elbow, MO: Elbow Inn. Great biker/roadie bar.
Lebanon, MO: Munger Moss Motel. Try to get into town at night so you can see the gorgeously lit sign. Better yet, stay there.
Strafford, MO: Exotic Animal Paradise.
Springfield, MO: Rest Haven Motel. I canıt personally vouch for the rooms, but the sign looks fantastic.
Carthage, MO: Route 66 Drive-In.
Galena, KS: Howard Litch Mining and Historical Museum.
Riverton, KS: Eisler Bros. General Store; Rainbow Bridge.
Miami, OK: Waylan's Ku-Ku. Have the fried green tomatoes.
Miami to Afton, OK: Sidewalk Highway.
Afton, OK: Afton Station. Stop and visit Laurel if she's there.
Foyil, OK: Four miles off 66 on OK 28A is the World's Largest Totem Pole.
Claremore, OK: J.M. Davis Museum; Cotton-Eyed Joe's barbecue.
Catoosa, OK: Blue Whale.
Tulsa, OK: Country Store; Lyon's Indian Store; Tally's Cafe; Cyrus Avery Route 66 Memorial Bridge; downtown Red Fork.
Depew, OK: Murals and historic buildings.
Stroud, OK: Shoe Tree; Rock Cafe. Have an order of fried pickles and a glass of sweet tea.
Chandler, OK: Restored Phillips 66 station; Museum of Pioneer History; spectacular mural at the west end of town.
Warwick, OK: Seaba Station. Be sure to visit Sue.
Arcadia, OK: Round barn.
Oklahoma City, OK: Cowboy Hall of Fame; County Line Barbecue; Lake Overholser Bridge; milk bottle building; Owl Courts; Western Trail Trading Post.
Yukon, OK: Yukon's Best Flour sign.
Bridgeport, OK: Pony truss bridge.
Hydro, OK: Lucille's.
Clinton, OK: McLain Rogers Park; Oklahoma Route 66 Museum.
Elk City, OK: National Route 66 Museum, Old Town Farm and Ranch Museum.
Just east of Erick, OK: Teally old alignment of 66 that you can drive on if you don't mind stopping to move branches out of the way every now and then.
Erick, OK: Visit Harley and Annabelle, tour the Roger Miller Museum, then cruise over to the West Winds Motel to see some cool vintage cars at a cool vintage motel. You can almost hear the ghosts whisper....
Texola, OK: Weird rusted-out sign in the middle of an empty field; old territorial jail just off 66.
Shamrock, TX: U-Drop-Inn.
McLean, TX: Devil's Rope Museum, restored Phillips 66 station.
Amarillo, TX: Big Texan Steak Ranch; Cadillac Ranch.
Vega, TX: Dotıs Mini-Museum; Libby's restaurant; Vega Motel.
Adrian, TX: Midpoint Cafe. Have a slice of pie.
Glenrio, TX/NM: Cool ghost town.
Tucumcari, NM: Blue Swallow Motel. DO NOT MISS UNDER ANY CIRCUMSTANCES. I'm serious. This is my hands-down favorite place on the entire road. Just positively gorgeous. While you're in town, buy souvenirs at Tepee Curios and cruise Tucumcari Boulevard to see the neon. Get up early the next morning after a good night's rest at the Blue Swallow and watch the sun rise over Tucumcari Mountain.
Santa Rosa, NM: Joseph's Cantina. Great breakfasts.
Cline's Corners, NM: World's most obnoxiously advertised truck stop. Blow some money on souvenirs.
Santa Fe, NM: The whole town is just plain gorgeous.
Between Santa Fe and Albuquerque, NM: La Bajada Hill. Allow a couple of extra hours to hike up the mesa and back down on a reeeeeeally old alignment of 66.
Moriarty, NM: El Comedor, home of the famous rotosphere (and a really killer posole recipe).
Albuquerque, NM: Neon everywhere you look; 66 Diner; lumberjack atop a building; and the Monterey, a terrific motel. It's a nonsmoking motel, so if you need your nic fix, you might want to look elsewhere ... but it's a great value. Lots of amenities, very clean, low prices, laundry on the premises.
Gallup, NM: El Rancho Hotel ("Home of the Stars") and lots of vintage neon.
Lupton, AZ: Indian trading posts galore on the NM/AZ border. Fantastic bargains for souvenir hunters.
East of Holbrook, AZ: Painted Desert. GORGEOUS.
Holbrook, AZ: Wigwam Motel; Joe & Aggie's restaurant.
Joseph City, AZ: HERE IT IS ... the most famous billboard on Route 66, at the Jack Rabbit Trading Post.
Twin Arrows, AZ: Twin Arrows. Dilapidated but still cool.
Flagstaff, AZ: Old alignment of 66 just west of town in the Kaibab National Forest. Now a nice hiking trail.
Winslow, AZ: Yeah, it's hopelessly dorky, but you know you want to do it, so go ahead ... have your picture taken "standin' on a corner in Winslow, Arizona." After all, dorky photo ops are what being a tourist is all about. ;) Then stay at La Posada for the evening, have breakfast in the Turquoise Room, and take note of the Valentine Diner down the street.
Meteor City, AZ: Worldıs Longest Map of Route 66, a geodesic dome with a rainbow on top, and boatloads of souvenirs.
Parks, AZ: Walking trail that used to be Route 66.
Seligman, AZ: Snow-Cap, Angel's Barbershop. Under no circumstances should you miss either of these attractions.
Hackberry, AZ: Hackberry General Store.
Oatman, AZ: Wild burros.
Needles, CA to Barstow, CA: Mojave Desert. Miles upon miles of nothing, which I find somehow oddly reassuring; rock graffiti; Roadrunner Cafe ruins.
Amboy, CA: Roy's.
Newberry Springs, CA: Bagdad Cafe. Mediocre food, but stop there anyway, just to say you did.
Ludlow, CA: Ludlow Cafe. Lousy service, good food, terrific building. Or at least, that was our experience.
Barstow, CA: Route 66 Mother Road Museum.
Victorville, CA: New Corral Motel. Gorgeous sign.
San Bernardino, CA: Wigwam Motel, Route 66/McDonald's museum.
Rancho Cucamonga, CA: Bono's Historic Orange.
Pasadena, CA: Fair Oaks Pharmacy. Have a chocolate malt.
Los Angeles, CA: Tons of great old motels, neon signs and other vestiges of the mid-20th century; end of the road.
Santa Monica, CA: Santa Monica Pier is just a bit past the end of Route 66 and is the symbolic end of the journey.