We visited Gubbio on the way from Assisi to Ancona. This seemed perhaps the oldest town we visited, judging from the age of the knight or saint in the church who died in 1040. There is a remnant of a Roman amphitheater in the meadow beneath the fortified city, that they now use for concerts.
Gubbio has historical roots dated back to the middle Paleolithic period, but became a significant part of the Umbrian empire in Pre-Roman Italy. The town, its piazza and churches (and their artwork) is beautifully preserved/restored, most of the entire town glowing in that burnt umber Italian hill town color that is immediately recognizable and lends an air so exotic yet so homey. We visited the Roman theatre, the Piazza Grande, the Church of San Francesco- still the most popular church in this region, and wandered the tiny stone streets.
We saw a wine barrel inside the building in which it was built, and havs never moved, as the building itself id part of the barrel’s structural integrity. It has no bands, just walls, keeping it together. It holds 193,000 something liters of wine. Now that was a party!