The first historical information about Montecarotto dates back to 1248 when Cardinal Raniero, Vicar of the Pope, confirmed the possession of the Castle of Montecarotto by the town council of Jesi. With the Marche Region annexed to the Kingdom of Italy, Montecarotto became the capital of Mandamento District.

The village has preserved a fine historical centre  and the old (1509) town wall which surrounds it. There are also two towers, of which one circular and the other polygonal.
At the top of the town, there is the Collegiata of the SS.  Announced (XV century), notable architecture reshaped in neoclassical style.
Just out of the wall in the S. Francesco Church (XVII century) we can admire a valuable organ by Pietro Nacchini (Istria), teacher of Gaetano Callido (author of the ancient organ dated back to 1788 in San Stefano Church in Maiolati Spontini).

Today, above all, Montecarotto is identified with the production of the famous wine Verdicchio Doc.

The Teatro Comunale was realized by Raffaele Grilli, an Italian architect (Jesi) and inaugurated in 1877.  After years of inactivity it has been recently reopened on the occasion of the Pergolesi Spontini Festival 2001. The Theatre has  stalls with curve in the form of horseshoe, and  three tiers of thirteen theatrical boxes. The decorations are by Giulio Marvardi.