Route 66 Motorcycle Tour - Chicago to Albuquerque (Guided)

The first half of Route 66, guided. Eight days from Chicago to Albuquerque, seven nights and around 1,525 miles, with a tour leader, an orientation briefing and a welcome dinner before the wheels turn.

Guided riding suits this half of the road particularly well. The eastern Route 66 is more about what sits beside it than the landscape it crosses, and the stops come in a planned sequence rather than by luck: the Pontiac museum, the Chain of Rocks Bridge over the Mississippi with its famous kink, the Gateway Arch at St Louis, the World’s Largest Rocking Chair at Fanning and Devil’s Elbow in the Ozarks.

More of the same follows across Oklahoma. The Blue Whale at Catoosa, a 1970s roadside swimming hole with a concrete whale in it, sits before Tulsa and Oklahoma City, then the Chisholm Trail and the Clinton Route 66 Museum lead to Amarillo. Santa Fe gets two nights, which is about right for its adobe streets, its galleries and its food, and a short 65-mile ride then finishes the trip in Albuquerque.

EAGLERIDER provides the motorcycle, the tour leader, all seven nights and the group dinners. Fuel, most meals and insurance are arranged separately. Riding days run from 65 to 335 miles across open plains country. For riders who want the Mother Road’s roadside Americana without having to work out which bits of the original alignment still exist and which have been swallowed by the interstate, this is the half where a guide genuinely earns their place.