Midwest Motorcycle Tour - 8 Day

The Midwest gets overlooked, which is most of this route’s appeal. Eight days out of Chicago, seven nights and around 1,050 miles, taking in the first stretch of Route 66, the Mississippi at St Louis, and a loop north through Wisconsin to Milwaukee.

It opens on the Mother Road itself, 205 miles through Braidwood and Pontiac to Springfield, then continues to St Louis over the Chain of Rocks Bridge, the old Route 66 crossing of the Mississippi with its famous kink in the middle. Cahokia Mounds sits nearby, the remains of a pre-Columbian city that was once larger than London and is now a set of enormous earthworks most people have never heard of.

The route then turns north. Hannibal comes first, where Mark Twain grew up and his boyhood home still stands, then Galesburg and on through Galena to Madison. Milwaukee follows, with Harley-Davidson’s Capitol Drive powertrain plant, and the final ride returns along Lake Michigan to Chicago.

EAGLERIDER supplies the motorcycle and books all seven nights, with Harley-Davidson touring models alongside Triumph and BMW sport machines. Fuel, meals and insurance are arranged separately. Days range from 95 to 290 miles on easy roads with light traffic. This is a week of American history rather than American scenery, and it is unusually good value for the distance. For riders who have done the deserts and want something with more in it than landscape, the Midwest tends to come as a genuine surprise, and this is a well-judged introduction to it.