Route 66 Centennial — 17-Day Self-Guided Motorcycle Tour
Celebrate the Mother Road with a 3,160-mile Chicago round trip through eight states. Ride Route 66 southwest to Albuquerque, then return through the San Juan Mountains, Colorado Rockies, Black Hills, Badlands, and Great Plains. The itinerary includes 14 riding days, 16 nights, and a rest day in Denver.
Start in Chicago at the traditional beginning of Route 66. The outbound journey follows the historic corridor through Joliet and Springfield to St. Louis, then continues across the Missouri Ozarks to Springfield, Missouri. Ride through Joplin and Catoosa to Tulsa, visit Arcadia and POPS on the way to Oklahoma City, and cross the Texas Panhandle past Shamrock and Cadillac Ranch to Amarillo.
Continue through Tucumcari and Santa Rosa to Santa Fe, then take the Turquoise Trail through Cerrillos and Madrid to Albuquerque. Instead of retracing the Mother Road, turn north on US-550 toward Durango and the San Juan Mountains.
The return is built around major mountain roads. Ride from Durango through Silverton to Ouray on the Million Dollar Highway, continue through Gunnison country to Aspen, and cross 12,095-foot Independence Pass to Denver. After a Denver rest day, make the 410-mile push through Wyoming to Rapid City.
The final stages cross Custer State Park and the Badlands to Sioux Falls, followed by a 490-mile ride through Minnesota and Wisconsin back to Chicago. These two long highway days balance the slower historic and mountain sections earlier in the tour.
Riders should prepare for desert heat, mountain passes above 12,000 feet, Great Plains thunderstorms, sparse fuel, seasonal snow closures, and limited cell coverage. The booklet recommends layers, waterproof gear, sun protection, offline maps, and early-morning mountain riding.
The outbound half emphasizes roadside history: original alignments, neon motor courts, diners, restored service stations, Route 66 museums, the Gateway Arch, the Blue Whale, POPS, Cadillac Ranch, Tucumcari, and New Mexico’s adobe cities. The return replaces roadside Americana with high mountain roads and national landscapes. Daily distances vary from 65 miles on the Turquoise Trail to 490 miles on the final transit day, so riders receive both slow exploration days and serious long-distance stages.
This is a self-guided tour. Booking the Experience includes a detailed booklet with the full itinerary, daily mileage, routes, scenic stops, dining and lodging suggestions, rider guidance, and Google Maps links.
17 Days · 3,160 Miles · Route 66 · San Juan Mountains · Rockies · Black Hills · Badlands · Self-Guided
