Route 66 Harley-Davidson Tour: Chicago to Santa Monica

Land at O'Hare by noon and take a taxi to the hotel. At 2 pm the van takes everyone to a Harley-Davidson dealer in the western suburbs for the handover: license check, seat and mirror fitting, saddlebags, a walk through the controls. Hank Delgado then runs the riding briefing on staggered formation, hand signals, fuel stops and what to do if a light splits the group. A shakedown ride of about 30 miles ends on Lake Shore Drive with the skyline ahead, followed by the welcome dinner.

An early start for a photo at the Begin Route 66 sign on Adams Street while the Loop is still quiet. Out along Ogden Avenue to Joliet, then two-lane road south through farm country. The Gemini Giant at Wilmington, the Polk-a-Dot Drive In at Braidwood with its fiberglass Elvis, Ambler's Texaco in Dwight and the murals of Pontiac fill the morning. Near Lexington you park the bikes and walk Memory Lane, a mile of original pavement lined with old billboards. About 210 miles to Springfield.

A shorter day, about 115 miles. South on the 1926 alignment through Auburn, where a stretch of red brick road still carries traffic, and Girard. Lunch in Carlinville by its outsized 1870 courthouse. The Chain of Rocks Bridge is closed to motor traffic, so the bikes park on the Illinois side and the group walks out to the famous bend above the Mississippi. Afternoon free in St. Louis, then an evening ride to Ted Drewes on Chippewa Street for frozen custard.

Out of St. Louis on Watson Road. Interstate 44 swallowed much of the Missouri road, but long sections survive beside it as quiet outer roads with real curves. The best comes after Rolla: Teardrop Road drops to Devils Elbow and its 1923 bridge over the Big Piney, then climbs through the Hooker Cut, a four-lane slot blasted through the ridge in the early 1940s. Fuel in Lebanon, a look at the Munger Moss sign, then Springfield. About 215 miles.

West out of Springfield through Halltown and past Gary's Gay Parita, a rebuilt Sinclair station, to Carthage and Joplin. Galena, in Kansas, has Cars on the Route in the old Kan-O-Tex station. South of Miami, Oklahoma, comes the Ribbon Road, laid in 1922 and only nine feet wide, with gravel shoulders. Hank leads it single file at about 30 mph. Then Afton, Vinita and Chelsea on a smooth two-lane, a pass by the Blue Whale of Catoosa, and Tulsa. About 185 miles.

From Tulsa the old road is two-lane nearly all the way to Oklahoma City, some of the best riding of the trip. Coffee at the Rock Cafe in Stroud, the Round Barn in Arcadia and a fuel stop at POPS. Lunch in El Reno is a fried onion burger, onions pressed into the patty on the griddle, a local habit since the Depression. Across the Canadian River at Bridgeport on the 38-span pony truss bridge of 1933, then Hydro, Weatherford and Clinton to Elk City. About 230 miles.

West of Elk City the land flattens and the wind rises, and Hank talks crosswinds over breakfast. Sayre and its domed courthouse, Erick, then Texola and into Texas. Shamrock for the green tile and neon of the U-Drop Inn, McLean for the Devil's Rope Museum and its barbed wire. In Groom, the leaning Britten water tower, then the last 40 miles into Amarillo. Dinner at the Big Texan is optional, and the 72-ounce steak is free if you finish it and its sides within an hour. About 150 miles.

Morning at Cadillac Ranch, where the 1974 cars wear a fresh coat of other people's spray paint every week. West on the frontage road through Vega, past its restored Magnolia station, to Adrian and lunch at the MidPoint Cafe. The old road to Glenrio and beyond turns to dirt near the state line, so the group takes the interstate for a stretch, then rejoins 66 at San Jon for the run into Tucumcari. Tonight is the Motel Safari, its sign topped by a camel. About 120 miles.

Santa Rosa first, about 60 miles, for the cold, clear Blue Hole and the Route 66 Auto Museum. Between Santa Rosa and Moriarty the 1937 road lies mostly under I-40, and this is the one long interstate stretch of the trip, about 90 miles with a break at Clines Corners. At Moriarty old 66 returns, climbs into Tijeras Canyon between the Sandia and Manzano mountains and drops onto Central Avenue. Hank is home here, and the evening ride under the neon is his to lead. About 175 miles.

A long day, about 270 miles. West across the Rio Grande and up Nine Mile Hill, past Laguna Pueblo and its white mission church, through Grants and over the Continental Divide at about 7,250 feet. Lunch at El Rancho in Gallup, the 1937 hotel that housed film crews. In Arizona, the 28-mile road through Petrified Forest National Park is easy curves, colored badlands and almost no traffic. Holbrook, then Winslow and the garden courtyard of La Posada for the night.

Up onto the Colorado Plateau through ponderosa pine to Flagstaff, near 7,000 feet and cool even in June. West of town old 66 returns in pieces at Parks and in Williams, where the bikes line the main street for lunch. From Ash Fork, Crookton Road carries the old highway to Seligman, and from there the longest surviving stretch runs with no stoplights past Peach Springs and the Hackberry General Store. Kingman by late afternoon. About 195 miles.

The day riders talk about later. From Kingman the Oatman Highway crosses open desert to Cool Springs, then climbs to Sitgreaves Pass, about 3,550 feet, in tight switchbacks without guardrails. Hank sets the rules over coffee: no passing, low gears, watch for burros. Oatman for a midmorning stop, then down to Topock and across the Colorado. West of Needles the National Trails Highway runs through Essex and Amboy, and fuel is planned with care, as stations sit far apart. Barstow by evening, about 210 miles.

The last ride. West of Barstow the old road follows the Mojave River through Helendale and Oro Grande, past Elmer's Bottle Tree Ranch, to Victorville. Down Cajon Pass, then Foothill Boulevard across the valley through Rialto and Rancho Cucamonga. Lane splitting is legal in California, but this group stays together in its lane. The photo at the End of the Trail sign on the Santa Monica Pier comes late in the afternoon, and the dealer collects the bikes at the hotel. Farewell dinner. About 140 miles.

No bike today, and most riders are glad of it for one morning. Breakfast, then time for the beach path, Palisades Park or a walk to Venice, about three miles south along the sand. LAX is about 10 miles from the hotel, 30 to 60 minutes depending on traffic, and a group transfer leaves at 10:30. If you want to keep riding, we can arrange a rental bike for a few extra days up the Pacific Coast Highway to Big Sur.