i’m still in Umbria, and over the past 2 days have visited more towns with cute streets, among their other charms. As mentioned above, Bevagna and Montefalco have nooks and crannies with evocative houses and streets. Bevagna is in the valley, rather than perched on a hilltop. It seems almost locked in the Middle Ages, and while the city has developed since Roman times, it still mostly has buildings that display a Medieval essence. The atmosphere is welcoming, where the town could’ve easily made themselves into a tourist trap instead, with such a magical and cute setting. As a bonus, parking is free, and there are lots of cats, which adds to the cuteness.
Montefalco has a rougher edge, and frankly, modern streets running between the old buildings detract from the potential cuteness factor. Many buildings have pastel colors as well as ancient stones - nice, but it’s not as cute as Bevagna, or as stony Spoleto.
But another town, an “11” on the cuteness meter, is Spello. Its Roman arch entry gate, modified in the Middle ages with homes built up against it, is a wonderful start. The 3-story high, rocky buildings lining every passageway, show it’s an old town in the middle of a big wine, olive oil, and black truffle/white truffle region. What sets Spello apart is the flowers and plants adorning most of the town, even in October. On the walls outside of homes are displayed tiles they’ve been awarded to announce the places they earned in the annual competition for the most attractive flower displays, gardens (very small gardens in a walled hilltown!), and window plant displays. The contest must be really competitive.