Going back to the Roman archeological sites (Villa San Paolo at Pozzarello, Vaiano and Segalare), on the slopes of Monte Albano.

The settlement of the castle of Monsummano Alto is documented from 1260, but probably existed since the previous century, or, as some have suggested due to the topology from the Lombard era.

The flat area was swampy (which can still be seen today through the Fucecchio Padule, close by), which became a human settlement in the second half of the 16th century with the construction of several farms and houses.

The lower section of the town dates mainly to the seventeenth century, when, after the miraculous apparition of the Virgin on 9 June 1573, the Grand Duke Ferdinand I of Tuscany started the construction of the Sanctuary of Our Lady of Fontenuova (1602-1605) as well as other buildings for the reception of pilgrims, such as Osteria dei Pellegrini, now the city's Museum.

The city, after a flow emigration with the advent of Fascism, became a place of immigration in the years 1951–61, mainly from southern Italy, passing rapidly from 9,708 residents (in 1951) to 11,631 (1961), due to the footwear sectors rise.