Route 66 Convertible Tour: Chicago to LA in a Classic Car

Arrive at O'Hare by early afternoon and take a taxi to the hotel, about 45 minutes. At 3 pm Mike Tillman, an Amarillo mechanic who has spent most of his working life on 1960s cars, walks you around the six convertibles in the hotel garage. The driving briefing covers drum brakes and longer stopping distances, the column shifter, the radio and how to raise the top in under a minute when rain comes. You choose a car, settle who drives first, then meet the group for the welcome dinner.

The convoy rolls at 7:30, before traffic thickens on Ogden Avenue. The first 40 miles are suburbs and stoplights, then the road opens into corn and soybean fields past Joliet. Swap drivers in Wilmington under the Gemini Giant, again at the Odell gas station, and again in Pontiac, with time for the murals and the Route 66 museum. Funks Grove sells maple sirup, spelled the old way, from a farm shed, and in Atlanta a giant holds a hot dog. About 210 miles to Springfield.

South through Mount Olive, where Soulsby's Shell station of 1926 sits restored beside the road. The cars park on the Illinois side of the Chain of Rocks Bridge and you walk out to the bend, with the river and the old water intake towers below, before driving across on the newer bridge. A quick run through St. Louis, then the old road southwest into the Ozark foothills. Tonight is the Wagon Wheel Motel in Cuba, stone cabins from 1936 under a neon sign. About 190 miles.

West of Cuba a rocking chair 42 feet tall stands at Fanning. The road then rolls over Ozark ridges, a good first test of those brakes, to Lebanon and on to Springfield, Missouri, where lunch is cashew chicken, a dish first served in the city in 1963. Afternoon on quiet farm roads through Halltown and Paris Springs to Carthage and its 1895 courthouse. Sleep at the Boots Court Motel, and if the 66 Drive-In Theatre is showing a film tonight, take a convertible. About 200 miles.

A short run through Joplin brings you into Kansas for its 13 miles. In Galena the old Kan-O-Tex station, now Cars on the Route, keeps the rusty tow truck that inspired a film character. A stop at Nelson's Old Riverton Store, a grocery since 1925, then Baxter Springs. Into Oklahoma through Commerce, where Mickey Mantle grew up, and Miami, home of the 1929 Coleman Theatre. You reach Tulsa by midafternoon, about 150 miles, with time to see the Meadow Gold sign lit on 11th Street.

Leave Tulsa past our office on 11th Street and stop in Sapulpa at the Heart of Route 66 Auto Museum, marked by a 66-foot gas pump. Lunch at the Rock Cafe in Stroud. Through Arcadia for the Round Barn and a fuel stop at POPS, then over the Canadian River at Bridgeport on a 1933 bridge of 38 pony trusses. Lucille's station in Hydro has stood by the road since 1929, and the Oklahoma Route 66 Museum in Clinton closes the day. About 230 miles, the longest drive so far.

Elk City's National Route 66 and Transportation Museum first, then west through Erick to Texola on the state line. In Shamrock, line the cars up in front of the U-Drop Inn, the 1936 Conoco station whose green tile and neon inspired a body shop in the film Cars. The Bug Ranch at Conway has five Volkswagen Beetles half buried in the dirt. Afternoon in Amarillo, which is Mike's hometown. Before sunset the six convertibles park beside the ten Cadillacs at Cadillac Ranch. About 150 miles.

A long day, about 280 miles and 9 hours. Lunch at the MidPoint Cafe in Adrian, halfway between Chicago and the Pacific. Past the ghost town of Glenrio into New Mexico, where the land breaks into mesas and the cars begin to climb. A photo stop under the Blue Swallow sign in Tucumcari, fuel in Santa Rosa, then the pre-1937 line of Route 66 north toward Santa Fe through piñon and juniper hills. By evening you are about 7,000 feet up, and the heater earns its keep with the top down.

A slow morning in Santa Fe: the Plaza, the spiral stair in Loretto Chapel and Native artists selling jewelry under the portal of the Palace of the Governors. Midday the convoy takes the interstate where the old road is gone, then picks up Central Avenue through Albuquerque, past the 1927 KiMo Theatre and El Vado Motel. West of the city Mike gathers everyone for photos at the 1933 Rio Puerco bridge, now closed to cars. Into Gallup by evening, about 205 miles, for a night at El Rancho.

A shorter day of about 130 miles, with the cars parked half the time. The 28-mile road through Petrified Forest National Park takes in the Painted Desert Inn, the Route 66 marker with its 1932 Studebaker, Blue Mesa and the quartz logs of Crystal Forest. Holbrook has the Wigwam Motel and its old cars out front, and in Joseph City the Jack Rabbit Trading Post billboard still says Here It Is. Winslow by late afternoon: the corner from the Eagles song, then La Posada and dinner at its Turquoise Room if you book.

West into ponderosa pine country. Coffee on the old road in downtown Flagstaff, then lunch in Williams, whose main street was the last piece of Route 66 bypassed by the interstate, in 1984. At Seligman the longest unbroken stretch of the old highway begins, about 158 miles to the Colorado River. Stop at Angel Delgadillo's barbershop and the Snow Cap next door, then let the convoy spread out across the Hualapai grasslands, past Peach Springs and the Hackberry General Store, to Kingman. About 195 miles.

Mike's favorite morning. Before the climb he goes over the plan: low gear on the column going up and coming down, no braking in the turns. The road rises in hairpins without guardrails to Sitgreaves Pass, about 3,550 feet, then drops into Oatman, where wild burros wander the street. Cross the Colorado River at Topock, refuel in Needles and drive the National Trails Highway west to Amboy, where Roy's sign has stood since 1959. Coffee at the Bagdad Cafe, then Barstow. About 210 miles.

Down Cajon Pass, a drop of roughly 3,000 feet in 25 miles, then west on Foothill Boulevard through the old citrus towns. Los Angeles traffic is part of the deal, so the convoy spaces out and the radios keep everyone together through Pasadena and Hollywood. The final miles run down Santa Monica Boulevard to Ocean Avenue. You hand the keys back to Mike at the hotel, walk to the End of the Trail sign on the pier, and meet for the farewell dinner. About 140 miles.

Breakfast, and the morning is yours: the beach path, Palisades Park on the bluff above the ocean, or the Third Street Promenade a few blocks inland. LAX is about 10 miles away, 30 to 60 minutes by taxi depending on traffic. If you booked flights with us, a transfer collects you at a time set for your departure. Anyone who wants more time on the coast can stay on, and we can add nights here or book a hotel in Malibu or Laguna Beach.