Joliet is not pretty and does not pretend to be, which is exactly why it makes a good Route 66 stop. It is an industrial city on the Des Plaines River, southwest of Chicago, with limestone quarries, steel mills, railway yards and a long history of making things and moving them. The old highway came through here on its way out of the metropolitan area, and the town still wears the road lightly, with a few vintage signs and diners and a welcome centre that tells you where to look.
The city is named for Louis Jolliet, the French-Canadian explorer who paddled through the region in 1673 with Father Marquette, searching for the Mississippi. The town started life under a different name and was renamed in the 1840s. The Illinois and Michigan Canal, which reached the town in the 1840s, linked the Great Lakes to the Mississippi system and made Joliet a transport hub, and the local limestone, quarried here in large amounts, ended up in buildings in Chicago and beyond. You can still see canal remnants and heritage trails.
Two landmarks stand out. The old state penitentiary, a huge, castle-like fortress in local limestone that opened in the middle of the nineteenth century, was closed in 2002 and is now partly open for tours, and film fans will recognise it from the opening of The Blues Brothers. The Rialto Square Theatre, built in 1926, is something else entirely, a gorgeous, over-the-top movie palace in Beaux-Arts style with chandeliers, marble and a ceiling worthy of a cathedral. Together they give you a fair summary of the town: tough and ornate in the same breath.
As for riding, you are still in the suburbs of a big city, so the old road is a mix of urban arterial, short stretches of quiet side street and the occasional bridge over the river. Traffic can be heavy on weekdays and the surfaces patchy, with frost damage from winters that come hard in northern Illinois. It is best taken as a gentle warm-up before the quieter, flatter country of the prairie to the south. Fuel and food are everywhere, with a large population of nearly a hundred and fifty thousand, so this is the place to prepare, grab breakfast and decide how many miles you really want to cover. Early spring and autumn are comfortable; summer humidity can be heavy.