Traces of a Roman road, Flaminia minor, joining Florentia with Felsina can still be found at the top of Mount Oggioli, approximately 8 kilometres (5 mi) south of town.

Due to its geographical position Monghidoro, which the writer Giordano Berti has described as the "Crossroads of Europe", in the course of the centuries became a necessary passage between the Po Valley and Central Italy.

The town, in its current form, originated in 1264 when the commune of Bologna created a vanguard here to counter the expansion of the Republic of Florence and in 1246, as a result of the complex politics of Italian city states of that period, the village was fortified to counter the continued border skirmishes and was given the nickname of Scaricalasino (in local Emilian Schirgalèṡen) which literally translates as "Unload the donkey"; this because the village sits at the top of a harsh ascent, which takes the traveller from 598 m to 841 m and it was indispensable to rest the beasts of burden following the climb.

From about 1660 until the advent of large-scale rail transit in the 1840s, Monghidoro was a mandatory stop-over to rest horses and carriage drivers of the aristocratic and fashionably polite society of the European continent on the Grand Tour of Italy on their way to Florence and Rome.

Badly damaged by allied bombings during World War II, the bell tower was pulled down soon after the conflict ended; In 1996, thanks to a large extent from funds raised by public and private enterprise, a recovery plan of what remains of the historic centre of Monghidoro was initiated.

Also at this time the local government decided to plant trees to beautify the square; this had the effect of spoiling the area, as the charm of the piazza had disappeared beneath the foliage.

In the 1990s, during the recovery plan, the trees were removed, the walls of the old church highlighted as well as the two narrow gaps at either end delimiting the piazza; new street lights were replaced with lanterns to give a turn of the century feel to the town.

The church, dedicated to the Virgin Mary, Patron Saint of Monghidoro, was built in 1951 from a drawing of architect Vignali; it was designed to replace the smaller chapel in the Cisterna complex deemed too small to accommodate the town needs.

The summit is reachable by car through dirt roads or on foot following marked trails where, on clear days, a scenic panorama, ranging from the Adriatic to the east and the Alps to the north, can be enjoyed.

For anyone wishing to gain a deeper knowledge of the many natural aspects of the Apennine, a didactical path has been predisposed allowing the visitor to observe the many species of the important diversity of plants in a woodland garden.

A number of mills used to provide an important source of income to the local area: an activity which lasted well into the 1950s was connected to the natural resources afforded by the proximity of the two rivers.

Today's local economy is largely based on commerce with tourism being common in the summer months; this is augmented by the very scenic SP65 thoroughfare, between Bologna and Florence, which attracts many foreign visitors on their tour through Italy.

Monghidoro is also renowned for its cakes; these are traditionally made with either wheat or chestnut flour then usually filled with fruits of the wood, jams and preserves, in the crostata style as well as apples, pears, figs, prunes, wholenuts, hazelnuts and pinenuts.