The main street of Montepulciano stretches for from the Porta al Prato to the Piazza Grande at the top of the hill.
The Cathedral of Santa Maria Assunta, or the Duomo of Montepulciano, constructed between 1594 and 1680, includes a masterpiece from the Sienese School, a massive Assumption of the Virgin triptych painted by Taddeo di Bartolo in 1401.