All activities / Motorcycle Adventure Touring / Route 66
Motorcycle Adventure Touring in Route 66US
The most famous road trip on earth: Chicago to Santa Monica across eight states and 3,900 kilometers of Americana, ridden on a Harley over about fifteen days.
Why here
Route 66 is the road trip other road trips are measured against: Chicago to Santa Monica across eight states, 3,900-plus kilometers of diners, deserts, neon, and Americana that riders from Europe and Australia rank as a lifetime goal. What makes it practical rather than mythical is the infrastructure: one-way Harley rental at scale, pick up in Chicago and drop in Los Angeles, exists here and almost nowhere else on earth, and guided operators run 15-day departures with support vans, luggage transfer, and hotels handled. The route threads Albuquerque and Grand Canyon country, so October riders can time the Balloon Fiesta on the way through.
Best months
May-June and September are the sweet spots; the high desert bakes in midsummer and the full season runs April to October. Guided tours want a motorcycle license and two years' riding; an international driving permit is recommended for overseas riders.
Getting there & around
Guided 15-day tours run Chicago to Los Angeles with half-route options; self-guided one-way rentals are widely available. Book December to March for the popular late-spring departures.
Skill levels: intermediate, advanced
Schools & guides (2)
EagleRider
OutfitterThe world's largest motorcycle rental and tour company, running guided and self-guided Route 66 trips with one-way Harley rentals between Chicago and Los Angeles.
Reuthers
OutfitterA tour operator running guided 15-day Harley-Davidson Route 66 tours with support vehicle and published annual departures.