Montecosaro is situated on a hill overlooking the valley of the river Chienti. It belongs to the association of The Most beautiful villages in Italy. The historic centre is surrounded by fourteenth-century walls. In central Piazza Trieste you can admire the nineteenth-century Teatro delle Logge, Palazzo Cesarini, and the Collegiate Church of San Lorenzo, featuring its original Romanesque bell tower and housing  a large wooden pre-Giotto crucifix.

Further historical monuments are: the Augustinian Complex, including the Church of Sant'Agostino, built around the middle of the thirteenth century, and the Town Hall, a former monastery of the Augustinians. The most remarkable tourist attraction is the basilica of “Santa Maria a piè di Chienti”, which is located in the village of Montecosaro Scalo. This small but perfectly formed 9th century double-decker church in the Chienti valley, just below Montecosaro, is surely the region's finest piece of Romanesque architecture. Its upper floor is built within the church at the far end of the high central nave. The 14th century frescoes in the apse above the upper altar are all the more powerful in their striking contrast with the remainder of the simple brick interior. Noteworthy are also the three side chapels built into the semi-circular apse of the lower church, which are among the few surviving examples of their kind in Italy.